Bihelović, Filip

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orcid::0000-0002-7654-3189
  • Bihelović, Filip (40)
Projects

Author's Bibliography

Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies

Ferjancic, Zorana; Bihelovic, Filip; Vulovic, Bojan; Matovic, Radomir; Trmcic, Milena; Jankovic, Aleksandar; Pavlovic, Milos; Djurkovic, Filip; Prodanovic, Radivoje; Djurdjevic Djelmas, Aleksandra; Kalicanin, Nevena; Zlatovic, Mario; Sladic, Dusan; Vallet, Thomas; Vignuzzi, Marco; Saicic, Radomir N.

(Taylor and Francis Group, 2024)

TY  - JOUR
AU  - Ferjancic, Zorana
AU  - Bihelovic, Filip
AU  - Vulovic, Bojan
AU  - Matovic, Radomir
AU  - Trmcic, Milena
AU  - Jankovic, Aleksandar
AU  - Pavlovic, Milos
AU  - Djurkovic, Filip
AU  - Prodanovic, Radivoje
AU  - Djurdjevic Djelmas, Aleksandra
AU  - Kalicanin, Nevena
AU  - Zlatovic, Mario
AU  - Sladic, Dusan
AU  - Vallet, Thomas
AU  - Vignuzzi, Marco
AU  - Saicic, Radomir N.
PY  - 2024
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/6475
AB  - We developed new iminosugar-based glycosidase inhibitors against SARS-CoV-2. Known drugs (miglustat, migalastat, miglitol, and swainsonine) were chosen as lead compounds to develop three classes of glycosidase inhibitors (α-glucosidase, α-galactosidase, and mannosidase). Molecular modelling of the lead compounds, synthesis of the compounds with the highest docking scores, enzyme inhibition tests, and in vitro antiviral assays afforded rationally designed inhibitors. Two highly active α-glucosidase inhibitors were discovered, where one of them is the most potent iminosugar-based anti-SARS-CoV-2 agent to date (EC90 = 1.94 µM in A549-ACE2 cells against Omicron BA.1 strain). However, galactosidase inhibitors did not exhibit antiviral activity, whereas mannosidase inhibitors were both active and cytotoxic. As our iminosugar-based drug candidates act by a host-directed mechanism, they should be more resilient to drug resistance. Moreover, this strategy could be extended to identify potential drug candidates for other viral infections.
PB  - Taylor and Francis Group
T2  - Journal of Enzyme Inhibition and Medicinal Chemistry
T1  - Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies
VL  - 39
IS  - 1
SP  - 2289007
DO  - 10.1080/14756366.2023.2289007
ER  - 
@article{
author = "Ferjancic, Zorana and Bihelovic, Filip and Vulovic, Bojan and Matovic, Radomir and Trmcic, Milena and Jankovic, Aleksandar and Pavlovic, Milos and Djurkovic, Filip and Prodanovic, Radivoje and Djurdjevic Djelmas, Aleksandra and Kalicanin, Nevena and Zlatovic, Mario and Sladic, Dusan and Vallet, Thomas and Vignuzzi, Marco and Saicic, Radomir N.",
year = "2024",
abstract = "We developed new iminosugar-based glycosidase inhibitors against SARS-CoV-2. Known drugs (miglustat, migalastat, miglitol, and swainsonine) were chosen as lead compounds to develop three classes of glycosidase inhibitors (α-glucosidase, α-galactosidase, and mannosidase). Molecular modelling of the lead compounds, synthesis of the compounds with the highest docking scores, enzyme inhibition tests, and in vitro antiviral assays afforded rationally designed inhibitors. Two highly active α-glucosidase inhibitors were discovered, where one of them is the most potent iminosugar-based anti-SARS-CoV-2 agent to date (EC90 = 1.94 µM in A549-ACE2 cells against Omicron BA.1 strain). However, galactosidase inhibitors did not exhibit antiviral activity, whereas mannosidase inhibitors were both active and cytotoxic. As our iminosugar-based drug candidates act by a host-directed mechanism, they should be more resilient to drug resistance. Moreover, this strategy could be extended to identify potential drug candidates for other viral infections.",
publisher = "Taylor and Francis Group",
journal = "Journal of Enzyme Inhibition and Medicinal Chemistry",
title = "Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies",
volume = "39",
number = "1",
pages = "2289007",
doi = "10.1080/14756366.2023.2289007"
}
Ferjancic, Z., Bihelovic, F., Vulovic, B., Matovic, R., Trmcic, M., Jankovic, A., Pavlovic, M., Djurkovic, F., Prodanovic, R., Djurdjevic Djelmas, A., Kalicanin, N., Zlatovic, M., Sladic, D., Vallet, T., Vignuzzi, M.,& Saicic, R. N.. (2024). Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies. in Journal of Enzyme Inhibition and Medicinal Chemistry
Taylor and Francis Group., 39(1), 2289007.
https://doi.org/10.1080/14756366.2023.2289007
Ferjancic Z, Bihelovic F, Vulovic B, Matovic R, Trmcic M, Jankovic A, Pavlovic M, Djurkovic F, Prodanovic R, Djurdjevic Djelmas A, Kalicanin N, Zlatovic M, Sladic D, Vallet T, Vignuzzi M, Saicic RN. Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies. in Journal of Enzyme Inhibition and Medicinal Chemistry. 2024;39(1):2289007.
doi:10.1080/14756366.2023.2289007 .
Ferjancic, Zorana, Bihelovic, Filip, Vulovic, Bojan, Matovic, Radomir, Trmcic, Milena, Jankovic, Aleksandar, Pavlovic, Milos, Djurkovic, Filip, Prodanovic, Radivoje, Djurdjevic Djelmas, Aleksandra, Kalicanin, Nevena, Zlatovic, Mario, Sladic, Dusan, Vallet, Thomas, Vignuzzi, Marco, Saicic, Radomir N., "Development of iminosugar-based glycosidase inhibitors as drug candidates for SARS-CoV-2 virus via molecular modelling and in vitro studies" in Journal of Enzyme Inhibition and Medicinal Chemistry, 39, no. 1 (2024):2289007,
https://doi.org/10.1080/14756366.2023.2289007 . .
4
1

Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence

Trajković, Miloš D.; Pavlović, Miloš; Bihelović, Filip; Ferjančić, Zorana; Saičić, Radomir

(SAGE Publications, 2022)

TY  - JOUR
AU  - Trajković, Miloš D.
AU  - Pavlović, Miloš
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2022
UR  - https://doi.org/10.1177/1934578X221091672
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5179
AB  - A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.
PB  - SAGE Publications
T2  - Natural Product Communications
T2  - Natural Product CommunicationsNatural Product Communications
T1  - Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence
VL  - 17
IS  - 4
DO  - 10.1177/1934578X221091672
ER  - 
@article{
author = "Trajković, Miloš D. and Pavlović, Miloš and Bihelović, Filip and Ferjančić, Zorana and Saičić, Radomir",
year = "2022",
abstract = "A tactical combination of either (S)- or (R)-proline catalyzed aldol reaction followed by intramolecular reductive amination enabled the synthesis of a chiral pyrrolidine derivative with 3 contiguous stereocenters in only 2 synthetic steps, starting from achiral precursors. This product, obtainable in both enantiomeric forms, was further exploited as a common intermediate in total syntheses of the biologically active iminosugars: ( + )-swainsonine, (–)-swainsonine, ( + )-8-epi-swainsonine, and ( + )-dideoxy-imino-lyxitol.",
publisher = "SAGE Publications",
journal = "Natural Product Communications, Natural Product CommunicationsNatural Product Communications",
title = "Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence",
volume = "17",
number = "4",
doi = "10.1177/1934578X221091672"
}
Trajković, M. D., Pavlović, M., Bihelović, F., Ferjančić, Z.,& Saičić, R.. (2022). Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence. in Natural Product Communications
SAGE Publications., 17(4).
https://doi.org/10.1177/1934578X221091672
Trajković MD, Pavlović M, Bihelović F, Ferjančić Z, Saičić R. Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence. in Natural Product Communications. 2022;17(4).
doi:10.1177/1934578X221091672 .
Trajković, Miloš D., Pavlović, Miloš, Bihelović, Filip, Ferjančić, Zorana, Saičić, Radomir, "Total Synthesis of ( + )-Swainsonine, (–)- Swainsonine, ( + )-8-epi-Swainsonine and ( + )- Dideoxy-Imino-Lyxitol by an Organocatalyzed Aldolization/Reductive Amination Sequence" in Natural Product Communications, 17, no. 4 (2022),
https://doi.org/10.1177/1934578X221091672 . .

Total Synthesis of (+)-Alstonlarsine A

Ferjančić, Zorana; Kukuruzar, Andrej ; Bihelović, Filip

(Wiley, 2022)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Kukuruzar, Andrej 
AU  - Bihelović, Filip
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5842
AB  - An enantioselective total synthesis of (+)-alstonlarsine A (1), a monoterpenoid indole alkaloid possessing a unique pentacyclic skeleton as well as a rare biological activity, is achieved. The key step is an efficient domino sequence, comprising enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels–Alder cycloaddition for the construction of 9-azatricyclo[4.3.1.03,8]decane core. The key intermediate for this domino sequence was synthesized by a newly developed methodology, relying on indole C(2)-H bond functionalization, combined with intramolecular Horner–Wadsworth–Emmons reaction. This tactical combination offers a new general entry into other (privileged) tricyclic frameworks possessing indole ring fused to 6-, 7- or 8-membered rings.
PB  - Wiley
T2  - Angewandte Chemie International Edition
T1  - Total Synthesis of (+)-Alstonlarsine A
VL  - 61
IS  - 39
SP  - e202210297
DO  - 10.1002/anie.202210297
ER  - 
@article{
author = "Ferjančić, Zorana and Kukuruzar, Andrej  and Bihelović, Filip",
year = "2022",
abstract = "An enantioselective total synthesis of (+)-alstonlarsine A (1), a monoterpenoid indole alkaloid possessing a unique pentacyclic skeleton as well as a rare biological activity, is achieved. The key step is an efficient domino sequence, comprising enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels–Alder cycloaddition for the construction of 9-azatricyclo[4.3.1.03,8]decane core. The key intermediate for this domino sequence was synthesized by a newly developed methodology, relying on indole C(2)-H bond functionalization, combined with intramolecular Horner–Wadsworth–Emmons reaction. This tactical combination offers a new general entry into other (privileged) tricyclic frameworks possessing indole ring fused to 6-, 7- or 8-membered rings.",
publisher = "Wiley",
journal = "Angewandte Chemie International Edition",
title = "Total Synthesis of (+)-Alstonlarsine A",
volume = "61",
number = "39",
pages = "e202210297",
doi = "10.1002/anie.202210297"
}
Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition
Wiley., 61(39), e202210297.
https://doi.org/10.1002/anie.202210297
Ferjančić Z, Kukuruzar A, Bihelović F. Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition. 2022;61(39):e202210297.
doi:10.1002/anie.202210297 .
Ferjančić, Zorana, Kukuruzar, Andrej , Bihelović, Filip, "Total Synthesis of (+)-Alstonlarsine A" in Angewandte Chemie International Edition, 61, no. 39 (2022):e202210297,
https://doi.org/10.1002/anie.202210297 . .
15
6
4
5

Total Synthesis of (+)-Alstonlarsine A

Ferjančić, Zorana; Kukuruzar, Andrej ; Bihelović, Filip

(Wiley, 2022)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Kukuruzar, Andrej 
AU  - Bihelović, Filip
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5843
AB  - An enantioselective total synthesis of (+)-alstonlarsine A (1), a monoterpenoid indole alkaloid possessing a unique pentacyclic skeleton as well as a rare biological activity, is achieved. The key step is an efficient domino sequence, comprising enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels–Alder cycloaddition for the construction of 9-azatricyclo[4.3.1.03,8]decane core. The key intermediate for this domino sequence was synthesized by a newly developed methodology, relying on indole C(2)-H bond functionalization, combined with intramolecular Horner–Wadsworth–Emmons reaction. This tactical combination offers a new general entry into other (privileged) tricyclic frameworks possessing indole ring fused to 6-, 7- or 8-membered rings.
PB  - Wiley
T2  - Angewandte Chemie International Edition
T1  - Total Synthesis of (+)-Alstonlarsine A
VL  - 61
IS  - 39
SP  - e202210297
DO  - 10.1002/anie.202210297
ER  - 
@article{
author = "Ferjančić, Zorana and Kukuruzar, Andrej  and Bihelović, Filip",
year = "2022",
abstract = "An enantioselective total synthesis of (+)-alstonlarsine A (1), a monoterpenoid indole alkaloid possessing a unique pentacyclic skeleton as well as a rare biological activity, is achieved. The key step is an efficient domino sequence, comprising enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels–Alder cycloaddition for the construction of 9-azatricyclo[4.3.1.03,8]decane core. The key intermediate for this domino sequence was synthesized by a newly developed methodology, relying on indole C(2)-H bond functionalization, combined with intramolecular Horner–Wadsworth–Emmons reaction. This tactical combination offers a new general entry into other (privileged) tricyclic frameworks possessing indole ring fused to 6-, 7- or 8-membered rings.",
publisher = "Wiley",
journal = "Angewandte Chemie International Edition",
title = "Total Synthesis of (+)-Alstonlarsine A",
volume = "61",
number = "39",
pages = "e202210297",
doi = "10.1002/anie.202210297"
}
Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition
Wiley., 61(39), e202210297.
https://doi.org/10.1002/anie.202210297
Ferjančić Z, Kukuruzar A, Bihelović F. Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition. 2022;61(39):e202210297.
doi:10.1002/anie.202210297 .
Ferjančić, Zorana, Kukuruzar, Andrej , Bihelović, Filip, "Total Synthesis of (+)-Alstonlarsine A" in Angewandte Chemie International Edition, 61, no. 39 (2022):e202210297,
https://doi.org/10.1002/anie.202210297 . .
15
6
3
5

Supplementary material for: Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition Wiley., 61(39), e202210297. https://doi.org/10.1002/anie.202210297

Ferjančić, Zorana; Kukuruzar, Andrej ; Bihelović, Filip

(Wiley, 2022)

TY  - DATA
AU  - Ferjančić, Zorana
AU  - Kukuruzar, Andrej 
AU  - Bihelović, Filip
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5844
AB  - An enantioselective total synthesis of (+)-alstonlarsine A (1), a monoterpenoid indole alkaloid possessing a unique pentacyclic skeleton as well as a rare biological activity, is achieved. The key step is an efficient domino sequence, comprising enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels–Alder cycloaddition for the construction of 9-azatricyclo[4.3.1.03,8]decane core. The key intermediate for this domino sequence was synthesized by a newly developed methodology, relying on indole C(2)-H bond functionalization, combined with intramolecular Horner–Wadsworth–Emmons reaction. This tactical combination offers a new general entry into other (privileged) tricyclic frameworks possessing indole ring fused to 6-, 7- or 8-membered rings.
PB  - Wiley
T2  - Angewandte Chemie International Edition
T1  - Supplementary material for: Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition Wiley., 61(39), e202210297. https://doi.org/10.1002/anie.202210297
VL  - 61
IS  - 39
SP  - e202210297
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5844
ER  - 
@misc{
author = "Ferjančić, Zorana and Kukuruzar, Andrej  and Bihelović, Filip",
year = "2022",
abstract = "An enantioselective total synthesis of (+)-alstonlarsine A (1), a monoterpenoid indole alkaloid possessing a unique pentacyclic skeleton as well as a rare biological activity, is achieved. The key step is an efficient domino sequence, comprising enamine formation followed by an inverse-electron-demand intramolecular dearomative Diels–Alder cycloaddition for the construction of 9-azatricyclo[4.3.1.03,8]decane core. The key intermediate for this domino sequence was synthesized by a newly developed methodology, relying on indole C(2)-H bond functionalization, combined with intramolecular Horner–Wadsworth–Emmons reaction. This tactical combination offers a new general entry into other (privileged) tricyclic frameworks possessing indole ring fused to 6-, 7- or 8-membered rings.",
publisher = "Wiley",
journal = "Angewandte Chemie International Edition",
title = "Supplementary material for: Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition Wiley., 61(39), e202210297. https://doi.org/10.1002/anie.202210297",
volume = "61",
number = "39",
pages = "e202210297",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5844"
}
Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Supplementary material for: Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition Wiley., 61(39), e202210297. https://doi.org/10.1002/anie.202210297. in Angewandte Chemie International Edition
Wiley., 61(39), e202210297.
https://hdl.handle.net/21.15107/rcub_cherry_5844
Ferjančić Z, Kukuruzar A, Bihelović F. Supplementary material for: Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition Wiley., 61(39), e202210297. https://doi.org/10.1002/anie.202210297. in Angewandte Chemie International Edition. 2022;61(39):e202210297.
https://hdl.handle.net/21.15107/rcub_cherry_5844 .
Ferjančić, Zorana, Kukuruzar, Andrej , Bihelović, Filip, "Supplementary material for: Ferjančić, Z., Kukuruzar, A.,& Bihelović, F.. (2022). Total Synthesis of (+)-Alstonlarsine A. in Angewandte Chemie International Edition Wiley., 61(39), e202210297. https://doi.org/10.1002/anie.202210297" in Angewandte Chemie International Edition, 61, no. 39 (2022):e202210297,
https://hdl.handle.net/21.15107/rcub_cherry_5844 .

Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A

Kukuruzar, Andrej; Bihelović, Filip; Ferjančić, Zorana

(Beograd : Srpsko hemijsko društvo, 2022)

TY  - CONF
AU  - Kukuruzar, Andrej
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5929
AB  - Jedan od ključnih koraka u okviru planirane totalne sinteze (+)-alstonlarsina A1 je 
intramolekulska Horner-Wadsworth-Emmons-ova (HWE) reakcija za zatvaranje 
cikloheptenskog prstena. Nedavno izolovani monoterpenski indolski alkaloid (+)-
alstonlarsin A poseduje jedinstvenu kavezastu strukturu, kao i biološki interesantnu 
osobinu da se ponaša kao inhibitor DRAK2 enzima. Stoga je razvijena nova metodologija 
za funkcionalizaciju indola u položaju 2, kako bi se sintetisao odgovarajući 2-
fosfonoacetatni indolski prekursor. Ova metodologija se zasniva na efikasnoj 
intramolekulskoj bakar-karbenoidnoj inserciji, čime je omogućena kasnija HWE reakcija i 
dobijanje kondenzovanih indolskih derivata sa kondenzovanim petočlanim, šestočlanim, 
sedmočlanim i osmočlanim prstenom.
AB  - One of the key steps in our efforts toward the total synthesis of (+)-alstonlarsine A1
 – a 
recently isolated monoterpenoid indole alkaloid possessing a unique cage-shaped structure 
and acting as Drak2 inhibitor – was an intramolecular Horner-Wadsworth-Emmons 
(HWE) reaction for the formation of the cycloheptene ring. To achieve this transformation, 
a new methodology for indole C-2 functionalization was developed aiming to synthesize 
the 2-phosphonoacetate indole precursor. The represented methodology relied on an 
efficient intermolecular copper carbenoid insertion, thus allowing a subsequent formation 
of indole derivatives with condensed 5-, 6-, 7- and 8-membered rings via HWE reaction.
PB  - Beograd : Srpsko hemijsko društvo
C3  - 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija
T1  - Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A
T1  - A copper carbenoid insertion/Horner-Wadsworth-Emmons reaction as a new method for the synthesis (+)-alstonlarsine A tricyclic core
VL  - 58
SP  - 133
EP  - 133
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5929
ER  - 
@conference{
author = "Kukuruzar, Andrej and Bihelović, Filip and Ferjančić, Zorana",
year = "2022",
abstract = "Jedan od ključnih koraka u okviru planirane totalne sinteze (+)-alstonlarsina A1 je 
intramolekulska Horner-Wadsworth-Emmons-ova (HWE) reakcija za zatvaranje 
cikloheptenskog prstena. Nedavno izolovani monoterpenski indolski alkaloid (+)-
alstonlarsin A poseduje jedinstvenu kavezastu strukturu, kao i biološki interesantnu 
osobinu da se ponaša kao inhibitor DRAK2 enzima. Stoga je razvijena nova metodologija 
za funkcionalizaciju indola u položaju 2, kako bi se sintetisao odgovarajući 2-
fosfonoacetatni indolski prekursor. Ova metodologija se zasniva na efikasnoj 
intramolekulskoj bakar-karbenoidnoj inserciji, čime je omogućena kasnija HWE reakcija i 
dobijanje kondenzovanih indolskih derivata sa kondenzovanim petočlanim, šestočlanim, 
sedmočlanim i osmočlanim prstenom., One of the key steps in our efforts toward the total synthesis of (+)-alstonlarsine A1
 – a 
recently isolated monoterpenoid indole alkaloid possessing a unique cage-shaped structure 
and acting as Drak2 inhibitor – was an intramolecular Horner-Wadsworth-Emmons 
(HWE) reaction for the formation of the cycloheptene ring. To achieve this transformation, 
a new methodology for indole C-2 functionalization was developed aiming to synthesize 
the 2-phosphonoacetate indole precursor. The represented methodology relied on an 
efficient intermolecular copper carbenoid insertion, thus allowing a subsequent formation 
of indole derivatives with condensed 5-, 6-, 7- and 8-membered rings via HWE reaction.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija",
title = "Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A, A copper carbenoid insertion/Horner-Wadsworth-Emmons reaction as a new method for the synthesis (+)-alstonlarsine A tricyclic core",
volume = "58",
pages = "133-133",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5929"
}
Kukuruzar, A., Bihelović, F.,& Ferjančić, Z.. (2022). Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A. in 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija
Beograd : Srpsko hemijsko društvo., 58, 133-133.
https://hdl.handle.net/21.15107/rcub_cherry_5929
Kukuruzar A, Bihelović F, Ferjančić Z. Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A. in 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija. 2022;58:133-133.
https://hdl.handle.net/21.15107/rcub_cherry_5929 .
Kukuruzar, Andrej, Bihelović, Filip, Ferjančić, Zorana, "Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A" in 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija, 58 (2022):133-133,
https://hdl.handle.net/21.15107/rcub_cherry_5929 .

Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova makrolinske/sarpaginske grupe alkaloida

Đurković, Filip T.; Ferjančić, Zorana; Bihelović, Filip

(Belgrade : Serbian Chemical Society, 2022)

TY  - CONF
AU  - Đurković, Filip T.
AU  - Ferjančić, Zorana
AU  - Bihelović, Filip
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5934
AB  - Indole alkaloid (+)-rauvomine B1
 contains cyclopropane ring incorporated in the 
unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this 
compound a challenging synthetic task. 
Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic 
intermediate, which could be efficiently prepared from commercially available N-Boc-(S)-
tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members 
of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate,
via unified strategy.
PB  - Belgrade : Serbian Chemical Society
C3  - 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine
T1  - Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova  makrolinske/sarpaginske grupe alkaloida
T1  - Synthetic studies towards (+)-rauvomine B and other  macroline/sarpagine alkaloids
IS  - 58
SP  - 134
EP  - 134
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5934
ER  - 
@conference{
author = "Đurković, Filip T. and Ferjančić, Zorana and Bihelović, Filip",
year = "2022",
abstract = "Indole alkaloid (+)-rauvomine B1
 contains cyclopropane ring incorporated in the 
unprecedented 6/5/6/6/3/5 hexacyclic structure ornate with six stereocenters, making this 
compound a challenging synthetic task. 
Our strategy for (+)-rauvomine B total synthesis proceeds via a key tetracyclic 
intermediate, which could be efficiently prepared from commercially available N-Boc-(S)-
tryptophan in 4 steps: 1) homologization to homotryptophan 2) aldol reaction 3) Pictet Spengler reaction 4) elimination. This efficient route also enabled several other members 
of macroline/sarpagine indole alkaloids to be synthesized from this common intermediate,
via unified strategy.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine",
title = "Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova  makrolinske/sarpaginske grupe alkaloida, Synthetic studies towards (+)-rauvomine B and other  macroline/sarpagine alkaloids",
number = "58",
pages = "134-134",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5934"
}
Đurković, F. T., Ferjančić, Z.,& Bihelović, F.. (2022). Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova  makrolinske/sarpaginske grupe alkaloida. in 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine
Belgrade : Serbian Chemical Society.(58), 134-134.
https://hdl.handle.net/21.15107/rcub_cherry_5934
Đurković FT, Ferjančić Z, Bihelović F. Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova  makrolinske/sarpaginske grupe alkaloida. in 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine. 2022;(58):134-134.
https://hdl.handle.net/21.15107/rcub_cherry_5934 .
Đurković, Filip T., Ferjančić, Zorana, Bihelović, Filip, "Sintetičke studije za dobijanje (+)-rauvomina B i drugih članova  makrolinske/sarpaginske grupe alkaloida" in 58. Savetovanje Srpskog hemijskog društva, Kratki izvodi radova, Beograd 9. i 10. jun 2022. godine, no. 58 (2022):134-134,
https://hdl.handle.net/21.15107/rcub_cherry_5934 .

Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A

Kukuruzar, Andrej; Bihelović, Filip; Ferjančić, Zorana

(Beograd : Srpsko hemijsko društvo, 2022)

TY  - CONF
AU  - Kukuruzar, Andrej
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
PY  - 2022
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/5930
AB  - Jedan od ključnih koraka u okviru planirane totalne sinteze (+)-alstonlarsina A1 je intramolekulska Horner-Wadsworth-Emmons-ova (HWE) reakcija za zatvaranje cikloheptenskog prstena. Nedavno izolovani monoterpenski indolski alkaloid (+)-alstonlarsin A poseduje jedinstvenu kavezastu strukturu, kao i biološki interesantnu osobinu da se ponaša kao inhibitor DRAK2 enzima. Stoga je razvijena nova metodologija za funkcionalizaciju indola u položaju 2, kako bi se sintetisao odgovarajući 2-fosfonoacetatni indolski prekursor. Ova metodologija se zasniva na efikasnoj intramolekulskoj bakar-karbenoidnoj inserciji, čime je omogućena kasnija HWE reakcija i dobijanje kondenzovanih indolskih derivata sa kondenzovanim petočlanim, šestočlanim, sedmočlanim i osmočlanim prstenom.
AB  - One of the key steps in our efforts toward the total synthesis of (+)-alstonlarsine A1 – a recently isolated monoterpenoid indole alkaloid possessing a unique cage-shaped structure and acting as Drak2 inhibitor – was an intramolecular Horner-Wadsworth-Emmons (HWE) reaction for the formation of the cycloheptene ring. To achieve this transformation, a new methodology for indole C-2 functionalization was developed aiming to synthesize the 2-phosphonoacetate indole precursor. The represented methodology relied on an efficient intermolecular copper carbenoid insertion, thus allowing a subsequent formation of indole derivatives with condensed 5-, 6-, 7- and 8-membered rings via HWE reaction.
PB  - Beograd : Srpsko hemijsko društvo
C3  - 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija
T1  - Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A
T1  - A copper carbenoid insertion/Horner-Wadsworth-Emmons reaction as a new method for the synthesis (+)-alstonlarsine A tricyclic core
VL  - 58
SP  - 133
EP  - 133
UR  - https://hdl.handle.net/21.15107/rcub_cherry_5930
ER  - 
@conference{
author = "Kukuruzar, Andrej and Bihelović, Filip and Ferjančić, Zorana",
year = "2022",
abstract = "Jedan od ključnih koraka u okviru planirane totalne sinteze (+)-alstonlarsina A1 je intramolekulska Horner-Wadsworth-Emmons-ova (HWE) reakcija za zatvaranje cikloheptenskog prstena. Nedavno izolovani monoterpenski indolski alkaloid (+)-alstonlarsin A poseduje jedinstvenu kavezastu strukturu, kao i biološki interesantnu osobinu da se ponaša kao inhibitor DRAK2 enzima. Stoga je razvijena nova metodologija za funkcionalizaciju indola u položaju 2, kako bi se sintetisao odgovarajući 2-fosfonoacetatni indolski prekursor. Ova metodologija se zasniva na efikasnoj intramolekulskoj bakar-karbenoidnoj inserciji, čime je omogućena kasnija HWE reakcija i dobijanje kondenzovanih indolskih derivata sa kondenzovanim petočlanim, šestočlanim, sedmočlanim i osmočlanim prstenom., One of the key steps in our efforts toward the total synthesis of (+)-alstonlarsine A1 – a recently isolated monoterpenoid indole alkaloid possessing a unique cage-shaped structure and acting as Drak2 inhibitor – was an intramolecular Horner-Wadsworth-Emmons (HWE) reaction for the formation of the cycloheptene ring. To achieve this transformation, a new methodology for indole C-2 functionalization was developed aiming to synthesize the 2-phosphonoacetate indole precursor. The represented methodology relied on an efficient intermolecular copper carbenoid insertion, thus allowing a subsequent formation of indole derivatives with condensed 5-, 6-, 7- and 8-membered rings via HWE reaction.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija",
title = "Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A, A copper carbenoid insertion/Horner-Wadsworth-Emmons reaction as a new method for the synthesis (+)-alstonlarsine A tricyclic core",
volume = "58",
pages = "133-133",
url = "https://hdl.handle.net/21.15107/rcub_cherry_5930"
}
Kukuruzar, A., Bihelović, F.,& Ferjančić, Z.. (2022). Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A. in 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija
Beograd : Srpsko hemijsko društvo., 58, 133-133.
https://hdl.handle.net/21.15107/rcub_cherry_5930
Kukuruzar A, Bihelović F, Ferjančić Z. Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A. in 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija. 2022;58:133-133.
https://hdl.handle.net/21.15107/rcub_cherry_5930 .
Kukuruzar, Andrej, Bihelović, Filip, Ferjančić, Zorana, "Insercija bakar-karbenoida/Horner-Wadsworth-Emmons-ova reakcija kao nova metoda za sintezu tricikličnog jezgra (+)-alstonlarsina A" in 58. Savetovanje Srpskog hemijskog društva: Kratki izvodi radova, 9. jun 2022, Beograd, Srbija, 58 (2022):133-133,
https://hdl.handle.net/21.15107/rcub_cherry_5930 .

Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone

Trajković, Milos; Ferjančić, Zorana; Saičić, Radomir; Bihelović, Filip

(Wiley, 2019)

TY  - JOUR
AU  - Trajković, Milos
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
AU  - Bihelović, Filip
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2869
AB  - A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ 6 - and Δ 7 -α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented.
PB  - Wiley
T2  - Chemistry - A European Journal
T1  - Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone
VL  - 25
IS  - 17
SP  - 4340
EP  - 4344
DO  - 10.1002/chem.201900497
ER  - 
@article{
author = "Trajković, Milos and Ferjančić, Zorana and Saičić, Radomir and Bihelović, Filip",
year = "2019",
abstract = "A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ 6 - and Δ 7 -α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented.",
publisher = "Wiley",
journal = "Chemistry - A European Journal",
title = "Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone",
volume = "25",
number = "17",
pages = "4340-4344",
doi = "10.1002/chem.201900497"
}
Trajković, M., Ferjančić, Z., Saičić, R.,& Bihelović, F.. (2019). Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. in Chemistry - A European Journal
Wiley., 25(17), 4340-4344.
https://doi.org/10.1002/chem.201900497
Trajković M, Ferjančić Z, Saičić R, Bihelović F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. in Chemistry - A European Journal. 2019;25(17):4340-4344.
doi:10.1002/chem.201900497 .
Trajković, Milos, Ferjančić, Zorana, Saičić, Radomir, Bihelović, Filip, "Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone" in Chemistry - A European Journal, 25, no. 17 (2019):4340-4344,
https://doi.org/10.1002/chem.201900497 . .
3
3
1
3
3

Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone

Trajković, Milos; Ferjančić, Zorana; Saičić, Radomir; Bihelović, Filip

(Wiley, 2019)

TY  - JOUR
AU  - Trajković, Milos
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
AU  - Bihelović, Filip
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2874
AB  - A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ 6 - and Δ 7 -α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented.
PB  - Wiley
T2  - Chemistry - A European Journal
T1  - Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone
VL  - 25
IS  - 17
SP  - 4340
EP  - 4344
DO  - 10.1002/chem.201900497
ER  - 
@article{
author = "Trajković, Milos and Ferjančić, Zorana and Saičić, Radomir and Bihelović, Filip",
year = "2019",
abstract = "A chiral-pool-based synthesis of the platensimycin core was achieved using (S)-lactic acid as an inexpensive starting material. The cyclohexenone ring was closed in a Mukaiyama–Michael domino sequence, while the quaternary stereocenter was created by a highly stereoselective decarboxylative allylation. The spirobicyclic skeleton was constructed by a RCM reaction. A new silver(I)-promoted cyclization reaction of Δ 6 - and Δ 7 -α-iodoketones was developed and applied for the pivotal carbon–carbon bond formation. The scope and limitations of this methodology are also presented.",
publisher = "Wiley",
journal = "Chemistry - A European Journal",
title = "Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone",
volume = "25",
number = "17",
pages = "4340-4344",
doi = "10.1002/chem.201900497"
}
Trajković, M., Ferjančić, Z., Saičić, R.,& Bihelović, F.. (2019). Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. in Chemistry - A European Journal
Wiley., 25(17), 4340-4344.
https://doi.org/10.1002/chem.201900497
Trajković M, Ferjančić Z, Saičić R, Bihelović F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. in Chemistry - A European Journal. 2019;25(17):4340-4344.
doi:10.1002/chem.201900497 .
Trajković, Milos, Ferjančić, Zorana, Saičić, Radomir, Bihelović, Filip, "Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone" in Chemistry - A European Journal, 25, no. 17 (2019):4340-4344,
https://doi.org/10.1002/chem.201900497 . .
3
3
1
3
3

Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A

Bihelović, Filip; Ferjančić, Zorana; Jončev, Zlatko

(Beograd : Srpsko hemijsko društvo, 2019)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
AU  - Jončev, Zlatko
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3660
AB  - Two new analogues of alstoscholarisine A, containing a phenyl or butyl substituent at the C-19 position, have been prepared in racemic form from the known skatole derivative. The syntheses of these compounds were accomplished in 13 steps, with a late-stage formation of the C-19 stereocenter. These derivatives are expected to have significantly changed biological activity, compared to alstoscholarisine A – a potent neuroactive natural product.
PB  - Beograd : Srpsko hemijsko društvo
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A
VL  - 84
IS  - 9
SP  - 935
EP  - 941
DO  - 10.2298/JSC190212026B
ER  - 
@article{
author = "Bihelović, Filip and Ferjančić, Zorana and Jončev, Zlatko",
year = "2019",
abstract = "Two new analogues of alstoscholarisine A, containing a phenyl or butyl substituent at the C-19 position, have been prepared in racemic form from the known skatole derivative. The syntheses of these compounds were accomplished in 13 steps, with a late-stage formation of the C-19 stereocenter. These derivatives are expected to have significantly changed biological activity, compared to alstoscholarisine A – a potent neuroactive natural product.",
publisher = "Beograd : Srpsko hemijsko društvo",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A",
volume = "84",
number = "9",
pages = "935-941",
doi = "10.2298/JSC190212026B"
}
Bihelović, F., Ferjančić, Z.,& Jončev, Z.. (2019). Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A. in Journal of the Serbian Chemical Society
Beograd : Srpsko hemijsko društvo., 84(9), 935-941.
https://doi.org/10.2298/JSC190212026B
Bihelović F, Ferjančić Z, Jončev Z. Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A. in Journal of the Serbian Chemical Society. 2019;84(9):935-941.
doi:10.2298/JSC190212026B .
Bihelović, Filip, Ferjančić, Zorana, Jončev, Zlatko, "Synthesis of two novel C-19 analogues of (±)-alstoscholarisine A" in Journal of the Serbian Chemical Society, 84, no. 9 (2019):935-941,
https://doi.org/10.2298/JSC190212026B . .
1
1
1

Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497

Trajković, Milos; Ferjančić, Zorana; Saičić, Radomir; Bihelović, Filip

(Wiley, 2019)

TY  - DATA
AU  - Trajković, Milos
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
AU  - Bihelović, Filip
PY  - 2019
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3842
PB  - Wiley
T2  - Chemistry - A European Journal
T1  - Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3842
ER  - 
@misc{
author = "Trajković, Milos and Ferjančić, Zorana and Saičić, Radomir and Bihelović, Filip",
year = "2019",
publisher = "Wiley",
journal = "Chemistry - A European Journal",
title = "Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3842"
}
Trajković, M., Ferjančić, Z., Saičić, R.,& Bihelović, F.. (2019). Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497. in Chemistry - A European Journal
Wiley..
https://hdl.handle.net/21.15107/rcub_cherry_3842
Trajković M, Ferjančić Z, Saičić R, Bihelović F. Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497. in Chemistry - A European Journal. 2019;.
https://hdl.handle.net/21.15107/rcub_cherry_3842 .
Trajković, Milos, Ferjančić, Zorana, Saičić, Radomir, Bihelović, Filip, "Supplementary data for the article: Trajkovic, M.; Ferjancic, Z.; Saicic, R. N.; Bihelovic, F. Enantioselective Synthesis of the Platensimycin Core by Silver(I)-Promoted Cyclization of Δ 6 -α-Iodoketone. Chemistry - A European Journal 2019, 25 (17), 4340–4344. https://doi.org/10.1002/chem.201900497" in Chemistry - A European Journal (2019),
https://hdl.handle.net/21.15107/rcub_cherry_3842 .

Gold(I)-Catalyzed C-O/C-C Bond-Forming Domino Reactions and Their Synthetic Applications

Bihelović, Filip; Vulović, Bojan; Saičić, Radomir

(Wiley-V C H Verlag Gmbh, Weinheim, 2018)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Vulović, Bojan
AU  - Saičić, Radomir
PY  - 2018
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2156
AB  - The advent of gold catalysis has transformed hydroxyalkoxylation of alkynes - once a rudimentary, mercury(II)-, or silver(I)-catalyzed process limited to structurally simple substrates - into a sophisticated method that has found application in syntheses of highly complex organic molecules. This transformation can further be combined with carbon-carbon bond-forming reactions into domino sequences that allow for a considerable increase of molecular complexity within a single synthetic step. Some recent examples of the development and synthetic applications of these reactions are provided.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Israel Journal of Chemistry
T1  - Gold(I)-Catalyzed C-O/C-C Bond-Forming Domino Reactions and Their Synthetic Applications
VL  - 58
IS  - 5
SP  - 521
EP  - 530
DO  - 10.1002/ijch.201700033
ER  - 
@article{
author = "Bihelović, Filip and Vulović, Bojan and Saičić, Radomir",
year = "2018",
abstract = "The advent of gold catalysis has transformed hydroxyalkoxylation of alkynes - once a rudimentary, mercury(II)-, or silver(I)-catalyzed process limited to structurally simple substrates - into a sophisticated method that has found application in syntheses of highly complex organic molecules. This transformation can further be combined with carbon-carbon bond-forming reactions into domino sequences that allow for a considerable increase of molecular complexity within a single synthetic step. Some recent examples of the development and synthetic applications of these reactions are provided.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Israel Journal of Chemistry",
title = "Gold(I)-Catalyzed C-O/C-C Bond-Forming Domino Reactions and Their Synthetic Applications",
volume = "58",
number = "5",
pages = "521-530",
doi = "10.1002/ijch.201700033"
}
Bihelović, F., Vulović, B.,& Saičić, R.. (2018). Gold(I)-Catalyzed C-O/C-C Bond-Forming Domino Reactions and Their Synthetic Applications. in Israel Journal of Chemistry
Wiley-V C H Verlag Gmbh, Weinheim., 58(5), 521-530.
https://doi.org/10.1002/ijch.201700033
Bihelović F, Vulović B, Saičić R. Gold(I)-Catalyzed C-O/C-C Bond-Forming Domino Reactions and Their Synthetic Applications. in Israel Journal of Chemistry. 2018;58(5):521-530.
doi:10.1002/ijch.201700033 .
Bihelović, Filip, Vulović, Bojan, Saičić, Radomir, "Gold(I)-Catalyzed C-O/C-C Bond-Forming Domino Reactions and Their Synthetic Applications" in Israel Journal of Chemistry, 58, no. 5 (2018):521-530,
https://doi.org/10.1002/ijch.201700033 . .
4
4
4
4

Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C

Bihelović, Filip; Vulović, Bojan; Saičić, Radomir

(Natural Products Inc, Westerville, 2017)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Vulović, Bojan
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2512
AB  - During our attempt to follow the planned synthetic route to the naturally occurring antibiotic (-)-atrop-abyssomicin C, we encountered two shortcomings, which forced us to reconsider our tactics and find new methods to overcome the problems. These methods turned out to be of general applicability, as demonstrated later in total syntheses of two other natural products: (+)-allokainic acid and (-)-gabosine H. The paper provides a brief account of these endeavors.
PB  - Natural Products Inc, Westerville
T2  - Natural Product Communications
T1  - Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C
VL  - 12
IS  - 8
SP  - 1209
EP  - 1214
UR  - https://hdl.handle.net/21.15107/rcub_cherry_2512
ER  - 
@article{
author = "Bihelović, Filip and Vulović, Bojan and Saičić, Radomir",
year = "2017",
abstract = "During our attempt to follow the planned synthetic route to the naturally occurring antibiotic (-)-atrop-abyssomicin C, we encountered two shortcomings, which forced us to reconsider our tactics and find new methods to overcome the problems. These methods turned out to be of general applicability, as demonstrated later in total syntheses of two other natural products: (+)-allokainic acid and (-)-gabosine H. The paper provides a brief account of these endeavors.",
publisher = "Natural Products Inc, Westerville",
journal = "Natural Product Communications",
title = "Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C",
volume = "12",
number = "8",
pages = "1209-1214",
url = "https://hdl.handle.net/21.15107/rcub_cherry_2512"
}
Bihelović, F., Vulović, B.,& Saičić, R.. (2017). Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C. in Natural Product Communications
Natural Products Inc, Westerville., 12(8), 1209-1214.
https://hdl.handle.net/21.15107/rcub_cherry_2512
Bihelović F, Vulović B, Saičić R. Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C. in Natural Product Communications. 2017;12(8):1209-1214.
https://hdl.handle.net/21.15107/rcub_cherry_2512 .
Bihelović, Filip, Vulović, Bojan, Saičić, Radomir, "Synthesis of Natural Products and the Development of Synthetic Methodology: The Case Study of (-)-Atrop-abyssomicin C" in Natural Product Communications, 12, no. 8 (2017):1209-1214,
https://hdl.handle.net/21.15107/rcub_cherry_2512 .
2
2

Total Synthesis of CrocaginA

Bihelović, Filip; Stichnoth, Desiree; Surup, Frank; Mueller, Rolf; Trauner, Dirk

(Wiley-V C H Verlag Gmbh, Weinheim, 2017)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Stichnoth, Desiree
AU  - Surup, Frank
AU  - Mueller, Rolf
AU  - Trauner, Dirk
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2532
AB  - CrocaginA (1) combines an attractive molecular structure with an unusual biosynthesis and bioactivity. An efficient synthesis of crocaginA is presented that hinges on an early formation of the heterotricyclic core, an electrophilic amination, and the stereoselective hydrogenation of a tetrasubstituted double bond. This synthesis confirms the absolute configuration of crocaginA and provides access to the natural product and derivatives thereof for further biological testing.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Angewandte Chemie (International Edition)
T1  - Total Synthesis of CrocaginA
VL  - 56
IS  - 42
SP  - 12848
EP  - 12851
DO  - 10.1002/anie.201612641
ER  - 
@article{
author = "Bihelović, Filip and Stichnoth, Desiree and Surup, Frank and Mueller, Rolf and Trauner, Dirk",
year = "2017",
abstract = "CrocaginA (1) combines an attractive molecular structure with an unusual biosynthesis and bioactivity. An efficient synthesis of crocaginA is presented that hinges on an early formation of the heterotricyclic core, an electrophilic amination, and the stereoselective hydrogenation of a tetrasubstituted double bond. This synthesis confirms the absolute configuration of crocaginA and provides access to the natural product and derivatives thereof for further biological testing.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Angewandte Chemie (International Edition)",
title = "Total Synthesis of CrocaginA",
volume = "56",
number = "42",
pages = "12848-12851",
doi = "10.1002/anie.201612641"
}
Bihelović, F., Stichnoth, D., Surup, F., Mueller, R.,& Trauner, D.. (2017). Total Synthesis of CrocaginA. in Angewandte Chemie (International Edition)
Wiley-V C H Verlag Gmbh, Weinheim., 56(42), 12848-12851.
https://doi.org/10.1002/anie.201612641
Bihelović F, Stichnoth D, Surup F, Mueller R, Trauner D. Total Synthesis of CrocaginA. in Angewandte Chemie (International Edition). 2017;56(42):12848-12851.
doi:10.1002/anie.201612641 .
Bihelović, Filip, Stichnoth, Desiree, Surup, Frank, Mueller, Rolf, Trauner, Dirk, "Total Synthesis of CrocaginA" in Angewandte Chemie (International Edition), 56, no. 42 (2017):12848-12851,
https://doi.org/10.1002/anie.201612641 . .
11
10
5
8
9

Supplementary material for the article: Bihelovic, F.; Stichnoth, D.; Surup, F.; Müller, R.; Trauner, D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition 2017, 56 (42), 12848–12851. https://doi.org/10.1002/anie.201612641

Bihelović, Filip; Stichnoth, Desiree; Surup, Frank; Müller, Rolf; Trauner, Dirk

(Wiley-V C H Verlag Gmbh, Weinheim, 2017)

TY  - DATA
AU  - Bihelović, Filip
AU  - Stichnoth, Desiree
AU  - Surup, Frank
AU  - Müller, Rolf
AU  - Trauner, Dirk
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3261
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Angewandte Chemie - International Edition
T1  - Supplementary material for the article: Bihelovic, F.; Stichnoth, D.; Surup, F.; Müller, R.; Trauner, D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition 2017, 56 (42), 12848–12851. https://doi.org/10.1002/anie.201612641
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3261
ER  - 
@misc{
author = "Bihelović, Filip and Stichnoth, Desiree and Surup, Frank and Müller, Rolf and Trauner, Dirk",
year = "2017",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Angewandte Chemie - International Edition",
title = "Supplementary material for the article: Bihelovic, F.; Stichnoth, D.; Surup, F.; Müller, R.; Trauner, D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition 2017, 56 (42), 12848–12851. https://doi.org/10.1002/anie.201612641",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3261"
}
Bihelović, F., Stichnoth, D., Surup, F., Müller, R.,& Trauner, D.. (2017). Supplementary material for the article: Bihelovic, F.; Stichnoth, D.; Surup, F.; Müller, R.; Trauner, D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition 2017, 56 (42), 12848–12851. https://doi.org/10.1002/anie.201612641. in Angewandte Chemie - International Edition
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3261
Bihelović F, Stichnoth D, Surup F, Müller R, Trauner D. Supplementary material for the article: Bihelovic, F.; Stichnoth, D.; Surup, F.; Müller, R.; Trauner, D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition 2017, 56 (42), 12848–12851. https://doi.org/10.1002/anie.201612641. in Angewandte Chemie - International Edition. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3261 .
Bihelović, Filip, Stichnoth, Desiree, Surup, Frank, Müller, Rolf, Trauner, Dirk, "Supplementary material for the article: Bihelovic, F.; Stichnoth, D.; Surup, F.; Müller, R.; Trauner, D. Total Synthesis of Crocagin A. Angewandte Chemie - International Edition 2017, 56 (42), 12848–12851. https://doi.org/10.1002/anie.201612641" in Angewandte Chemie - International Edition (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3261 .

Total Synthesis of (+/-)-Alstoscholarisine A

Bihelović, Filip; Ferjančić, Zorana

(Georg Thieme Verlag Kg, Stuttgart, 2016)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1927
PB  - Georg Thieme Verlag Kg, Stuttgart
T2  - Synlett
T1  - Total Synthesis of (+/-)-Alstoscholarisine A
VL  - 27
IS  - 8
UR  - https://hdl.handle.net/21.15107/rcub_cherry_1927
ER  - 
@article{
author = "Bihelović, Filip and Ferjančić, Zorana",
year = "2016",
publisher = "Georg Thieme Verlag Kg, Stuttgart",
journal = "Synlett",
title = "Total Synthesis of (+/-)-Alstoscholarisine A",
volume = "27",
number = "8",
url = "https://hdl.handle.net/21.15107/rcub_cherry_1927"
}
Bihelović, F.,& Ferjančić, Z.. (2016). Total Synthesis of (+/-)-Alstoscholarisine A. in Synlett
Georg Thieme Verlag Kg, Stuttgart., 27(8).
https://hdl.handle.net/21.15107/rcub_cherry_1927
Bihelović F, Ferjančić Z. Total Synthesis of (+/-)-Alstoscholarisine A. in Synlett. 2016;27(8).
https://hdl.handle.net/21.15107/rcub_cherry_1927 .
Bihelović, Filip, Ferjančić, Zorana, "Total Synthesis of (+/-)-Alstoscholarisine A" in Synlett, 27, no. 8 (2016),
https://hdl.handle.net/21.15107/rcub_cherry_1927 .

Total Synthesis of (+/-)-Alstoscholarisine A

Bihelović, Filip; Ferjančić, Zorana

(Wiley-V C H Verlag Gmbh, Weinheim, 2016)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2048
AB  - The first total synthesis of the neuroactive indole alkaloid (+/-)-alstoscholarisine A is reported. The key step of the concise synthesis is an efficient domino sequence that was used to assemble the 2,8-diazabicyclo[3.3.1]nonane core through the formation of two C-N bonds and one C-C bond in a single step.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Angewandte Chemie (International Edition)
T1  - Total Synthesis of (+/-)-Alstoscholarisine A
VL  - 55
IS  - 7
SP  - 2569
EP  - 2572
DO  - 10.1002/anie.201510777
ER  - 
@article{
author = "Bihelović, Filip and Ferjančić, Zorana",
year = "2016",
abstract = "The first total synthesis of the neuroactive indole alkaloid (+/-)-alstoscholarisine A is reported. The key step of the concise synthesis is an efficient domino sequence that was used to assemble the 2,8-diazabicyclo[3.3.1]nonane core through the formation of two C-N bonds and one C-C bond in a single step.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Angewandte Chemie (International Edition)",
title = "Total Synthesis of (+/-)-Alstoscholarisine A",
volume = "55",
number = "7",
pages = "2569-2572",
doi = "10.1002/anie.201510777"
}
Bihelović, F.,& Ferjančić, Z.. (2016). Total Synthesis of (+/-)-Alstoscholarisine A. in Angewandte Chemie (International Edition)
Wiley-V C H Verlag Gmbh, Weinheim., 55(7), 2569-2572.
https://doi.org/10.1002/anie.201510777
Bihelović F, Ferjančić Z. Total Synthesis of (+/-)-Alstoscholarisine A. in Angewandte Chemie (International Edition). 2016;55(7):2569-2572.
doi:10.1002/anie.201510777 .
Bihelović, Filip, Ferjančić, Zorana, "Total Synthesis of (+/-)-Alstoscholarisine A" in Angewandte Chemie (International Edition), 55, no. 7 (2016):2569-2572,
https://doi.org/10.1002/anie.201510777 . .
13
22
13
20
20

Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H

Vulović, Bojan; Kolarski, Dušan; Bihelović, Filip; Matović, Radomir; Gruden-Pavlović, Maja; Saičić, Radomir

(Amer Chemical Soc, Washington, 2016)

TY  - JOUR
AU  - Vulović, Bojan
AU  - Kolarski, Dušan
AU  - Bihelović, Filip
AU  - Matović, Radomir
AU  - Gruden-Pavlović, Maja
AU  - Saičić, Radomir
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2290
AB  - 1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer.
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H
VL  - 18
IS  - 15
SP  - 3886
EP  - 3889
DO  - 10.1021/acs.orglett.6b01898
ER  - 
@article{
author = "Vulović, Bojan and Kolarski, Dušan and Bihelović, Filip and Matović, Radomir and Gruden-Pavlović, Maja and Saičić, Radomir",
year = "2016",
abstract = "1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer.",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H",
volume = "18",
number = "15",
pages = "3886-3889",
doi = "10.1021/acs.orglett.6b01898"
}
Vulović, B., Kolarski, D., Bihelović, F., Matović, R., Gruden-Pavlović, M.,& Saičić, R.. (2016). Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H. in Organic Letters
Amer Chemical Soc, Washington., 18(15), 3886-3889.
https://doi.org/10.1021/acs.orglett.6b01898
Vulović B, Kolarski D, Bihelović F, Matović R, Gruden-Pavlović M, Saičić R. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H. in Organic Letters. 2016;18(15):3886-3889.
doi:10.1021/acs.orglett.6b01898 .
Vulović, Bojan, Kolarski, Dušan, Bihelović, Filip, Matović, Radomir, Gruden-Pavlović, Maja, Saičić, Radomir, "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H" in Organic Letters, 18, no. 15 (2016):3886-3889,
https://doi.org/10.1021/acs.orglett.6b01898 . .
10
17
11
18
14

Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (vol 18, pg 3886, 2016)

Vulović, Bojan; Kolarski, Dušan; Bihelović, Filip; Matović, Radomir; Gruden-Pavlović, Maja; Saičić, Radomir

(Amer Chemical Soc, Washington, 2016)

TY  - JOUR
AU  - Vulović, Bojan
AU  - Kolarski, Dušan
AU  - Bihelović, Filip
AU  - Matović, Radomir
AU  - Gruden-Pavlović, Maja
AU  - Saičić, Radomir
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2327
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (vol 18, pg 3886, 2016)
VL  - 18
IS  - 19
SP  - 5186
EP  - 5187
DO  - 10.1021/acs.orglett.6b02509
ER  - 
@article{
author = "Vulović, Bojan and Kolarski, Dušan and Bihelović, Filip and Matović, Radomir and Gruden-Pavlović, Maja and Saičić, Radomir",
year = "2016",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (vol 18, pg 3886, 2016)",
volume = "18",
number = "19",
pages = "5186-5187",
doi = "10.1021/acs.orglett.6b02509"
}
Vulović, B., Kolarski, D., Bihelović, F., Matović, R., Gruden-Pavlović, M.,& Saičić, R.. (2016). Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (vol 18, pg 3886, 2016). in Organic Letters
Amer Chemical Soc, Washington., 18(19), 5186-5187.
https://doi.org/10.1021/acs.orglett.6b02509
Vulović B, Kolarski D, Bihelović F, Matović R, Gruden-Pavlović M, Saičić R. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (vol 18, pg 3886, 2016). in Organic Letters. 2016;18(19):5186-5187.
doi:10.1021/acs.orglett.6b02509 .
Vulović, Bojan, Kolarski, Dušan, Bihelović, Filip, Matović, Radomir, Gruden-Pavlović, Maja, Saičić, Radomir, "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H (vol 18, pg 3886, 2016)" in Organic Letters, 18, no. 19 (2016):5186-5187,
https://doi.org/10.1021/acs.orglett.6b02509 . .
1
2
1

Supplementary data for the article: Vulovic, B.; Kolarski, D.; Bihelovic, F.; Matovic, R.; Gruden, M.; Saicic, R. N. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-Epi-Gabosine H. Organic Letters 2016, 18 (15), 3886–3889. https://doi.org/10.1021/acs.orglett.6b01898

Vulović, Bojan; Kolarski, Dušan; Bihelović, Filip; Matović, Radomir; Gruden-Pavlović, Maja; Saičić, Radomir

(Amer Chemical Soc, Washington, 2016)

TY  - DATA
AU  - Vulović, Bojan
AU  - Kolarski, Dušan
AU  - Bihelović, Filip
AU  - Matović, Radomir
AU  - Gruden-Pavlović, Maja
AU  - Saičić, Radomir
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3520
PB  - Amer Chemical Soc, Washington
T2  - Organic Letters
T1  - Supplementary data for the article: Vulovic, B.; Kolarski, D.; Bihelovic, F.; Matovic, R.; Gruden, M.; Saicic, R. N. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-Epi-Gabosine H. Organic Letters 2016, 18 (15), 3886–3889. https://doi.org/10.1021/acs.orglett.6b01898
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3520
ER  - 
@misc{
author = "Vulović, Bojan and Kolarski, Dušan and Bihelović, Filip and Matović, Radomir and Gruden-Pavlović, Maja and Saičić, Radomir",
year = "2016",
publisher = "Amer Chemical Soc, Washington",
journal = "Organic Letters",
title = "Supplementary data for the article: Vulovic, B.; Kolarski, D.; Bihelovic, F.; Matovic, R.; Gruden, M.; Saicic, R. N. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-Epi-Gabosine H. Organic Letters 2016, 18 (15), 3886–3889. https://doi.org/10.1021/acs.orglett.6b01898",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3520"
}
Vulović, B., Kolarski, D., Bihelović, F., Matović, R., Gruden-Pavlović, M.,& Saičić, R.. (2016). Supplementary data for the article: Vulovic, B.; Kolarski, D.; Bihelovic, F.; Matovic, R.; Gruden, M.; Saicic, R. N. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-Epi-Gabosine H. Organic Letters 2016, 18 (15), 3886–3889. https://doi.org/10.1021/acs.orglett.6b01898. in Organic Letters
Amer Chemical Soc, Washington..
https://hdl.handle.net/21.15107/rcub_cherry_3520
Vulović B, Kolarski D, Bihelović F, Matović R, Gruden-Pavlović M, Saičić R. Supplementary data for the article: Vulovic, B.; Kolarski, D.; Bihelovic, F.; Matovic, R.; Gruden, M.; Saicic, R. N. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-Epi-Gabosine H. Organic Letters 2016, 18 (15), 3886–3889. https://doi.org/10.1021/acs.orglett.6b01898. in Organic Letters. 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3520 .
Vulović, Bojan, Kolarski, Dušan, Bihelović, Filip, Matović, Radomir, Gruden-Pavlović, Maja, Saičić, Radomir, "Supplementary data for the article: Vulovic, B.; Kolarski, D.; Bihelovic, F.; Matovic, R.; Gruden, M.; Saicic, R. N. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-Epi-Gabosine H. Organic Letters 2016, 18 (15), 3886–3889. https://doi.org/10.1021/acs.orglett.6b01898" in Organic Letters (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3520 .

Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777

Bihelović, Filip; Ferjančić, Zorana

(Wiley-V C H Verlag Gmbh, Weinheim, 2016)

TY  - DATA
AU  - Bihelović, Filip
AU  - Ferjančić, Zorana
PY  - 2016
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3655
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - Angewandte Chemie (International Edition)
T1  - Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3655
ER  - 
@misc{
author = "Bihelović, Filip and Ferjančić, Zorana",
year = "2016",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "Angewandte Chemie (International Edition)",
title = "Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3655"
}
Bihelović, F.,& Ferjančić, Z.. (2016). Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777. in Angewandte Chemie (International Edition)
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3655
Bihelović F, Ferjančić Z. Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777. in Angewandte Chemie (International Edition). 2016;.
https://hdl.handle.net/21.15107/rcub_cherry_3655 .
Bihelović, Filip, Ferjančić, Zorana, "Supplementary data for the article: Bihelovic, F.; Ferjancic, Z. Total Synthesis of (±)-Alstoscholarisine A. Angewandte Chemie - International Edition 2016, 55 (7), 2569–2572. https://doi.org/10.1002/anie.201510777" in Angewandte Chemie (International Edition) (2016),
https://hdl.handle.net/21.15107/rcub_cherry_3655 .

Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen

Novković, Luka P.; Trmčić, Milena; Rodić, Marko; Bihelović, Filip; Zlatar, Matija; Matović, Radomir; Saičić, Radomir

(Royal Soc Chemistry, Cambridge, 2015)

TY  - JOUR
AU  - Novković, Luka P.
AU  - Trmčić, Milena
AU  - Rodić, Marko
AU  - Bihelović, Filip
AU  - Zlatar, Matija
AU  - Matović, Radomir
AU  - Saičić, Radomir
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2000
AB  - Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen
VL  - 5
IS  - 120
SP  - 99577
EP  - 99584
DO  - 10.1039/c5ra13476e
ER  - 
@article{
author = "Novković, Luka P. and Trmčić, Milena and Rodić, Marko and Bihelović, Filip and Zlatar, Matija and Matović, Radomir and Saičić, Radomir",
year = "2015",
abstract = "Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen",
volume = "5",
number = "120",
pages = "99577-99584",
doi = "10.1039/c5ra13476e"
}
Novković, L. P., Trmčić, M., Rodić, M., Bihelović, F., Zlatar, M., Matović, R.,& Saičić, R.. (2015). Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(120), 99577-99584.
https://doi.org/10.1039/c5ra13476e
Novković LP, Trmčić M, Rodić M, Bihelović F, Zlatar M, Matović R, Saičić R. Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances. 2015;5(120):99577-99584.
doi:10.1039/c5ra13476e .
Novković, Luka P., Trmčić, Milena, Rodić, Marko, Bihelović, Filip, Zlatar, Matija, Matović, Radomir, Saičić, Radomir, "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen" in RSC Advances, 5, no. 120 (2015):99577-99584,
https://doi.org/10.1039/c5ra13476e . .
10
6
9
10

Supplementary data for article: Novkovic, L.; Trmcic, M.; Rodic, M.; Bihelovic, F.; Zlatar, M.; Matovic, R.; Saicic, R. N. Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen. RSC Advances 2015, 5 (120), 99577–99584. https://doi.org/10.1039/c5ra13476e

Novković, Luka P.; Trmčić, Milena; Rodić, Marko; Bihelović, Filip; Zlatar, Matija; Matović, Radomir; Saičić, Radomir

(Royal Soc Chemistry, Cambridge, 2015)

TY  - DATA
AU  - Novković, Luka P.
AU  - Trmčić, Milena
AU  - Rodić, Marko
AU  - Bihelović, Filip
AU  - Zlatar, Matija
AU  - Matović, Radomir
AU  - Saičić, Radomir
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3442
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Supplementary data for article: Novkovic, L.; Trmcic, M.; Rodic, M.; Bihelovic, F.; Zlatar, M.; Matovic, R.; Saicic, R. N. Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen. RSC Advances 2015, 5 (120), 99577–99584. https://doi.org/10.1039/c5ra13476e
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3442
ER  - 
@misc{
author = "Novković, Luka P. and Trmčić, Milena and Rodić, Marko and Bihelović, Filip and Zlatar, Matija and Matović, Radomir and Saičić, Radomir",
year = "2015",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Supplementary data for article: Novkovic, L.; Trmcic, M.; Rodic, M.; Bihelovic, F.; Zlatar, M.; Matovic, R.; Saicic, R. N. Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen. RSC Advances 2015, 5 (120), 99577–99584. https://doi.org/10.1039/c5ra13476e",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3442"
}
Novković, L. P., Trmčić, M., Rodić, M., Bihelović, F., Zlatar, M., Matović, R.,& Saičić, R.. (2015). Supplementary data for article: Novkovic, L.; Trmcic, M.; Rodic, M.; Bihelovic, F.; Zlatar, M.; Matovic, R.; Saicic, R. N. Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen. RSC Advances 2015, 5 (120), 99577–99584. https://doi.org/10.1039/c5ra13476e. in RSC Advances
Royal Soc Chemistry, Cambridge..
https://hdl.handle.net/21.15107/rcub_cherry_3442
Novković LP, Trmčić M, Rodić M, Bihelović F, Zlatar M, Matović R, Saičić R. Supplementary data for article: Novkovic, L.; Trmcic, M.; Rodic, M.; Bihelovic, F.; Zlatar, M.; Matovic, R.; Saicic, R. N. Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen. RSC Advances 2015, 5 (120), 99577–99584. https://doi.org/10.1039/c5ra13476e. in RSC Advances. 2015;.
https://hdl.handle.net/21.15107/rcub_cherry_3442 .
Novković, Luka P., Trmčić, Milena, Rodić, Marko, Bihelović, Filip, Zlatar, Matija, Matović, Radomir, Saičić, Radomir, "Supplementary data for article: Novkovic, L.; Trmcic, M.; Rodic, M.; Bihelovic, F.; Zlatar, M.; Matovic, R.; Saicic, R. N. Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen. RSC Advances 2015, 5 (120), 99577–99584. https://doi.org/10.1039/c5ra13476e" in RSC Advances (2015),
https://hdl.handle.net/21.15107/rcub_cherry_3442 .

The specificity of alpha-glucosidase from Saccharomyces cerevisiae differs depending on the type of reaction: hydrolysis versus transglucosylation

Dusan, Velickovic; Nenad, Milosavic; Dejan, Bezbradica; Bihelović, Filip; Segal, Ann Marie; Šegan, Dejan M.; Trbojević-Ivić, Jovana; Aleksandra, Dimitrijevic

(Springer, New York, 2014)

TY  - JOUR
AU  - Dusan, Velickovic
AU  - Nenad, Milosavic
AU  - Dejan, Bezbradica
AU  - Bihelović, Filip
AU  - Segal, Ann Marie
AU  - Šegan, Dejan M.
AU  - Trbojević-Ivić, Jovana
AU  - Aleksandra, Dimitrijevic
PY  - 2014
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1797
AB  - Our investigation of the catalytic properties of Saccharomyces cerevisiae alpha-glucosidase (AGL) using hydroxybenzyl alcohol (HBA) isomers as transglucosylation substrates and their glucosides in hydrolytic reactions demonstrated interesting findings pertaining to the aglycon specificity of this important enzyme. AGL specificity increased from the para(p)- to the ortho(o)-HBA isomer in transglucosylation, whereas such AGL aglycon specificity was not seen in hydrolysis, thus indicating that the second step of the reaction (i.e., binding of the glucosyl acceptor) is rate-determining. To study the influence of substitution pattern on AGL kinetics, we compared AGL specificity, inferred from kinetic constants, for HBA isomers and other aglycon substrates. The demonstrated inhibitory effects of HBA isomers and their corresponding glucosides on AGL-catalyzed hydrolysis of p-nitrophenyl a-glucoside (PNPG) suggest that HBA glucosides act as competitive, whereas HBA isomers are noncompetitive, inhibitors. As such, we postulate that aromatic moieties cannot bind to an active site unless an enzyme-glucosyl complex has already formed, but they can interact with other regions of the enzyme molecule resulting in inhibition.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - The specificity of alpha-glucosidase from Saccharomyces cerevisiae differs depending on the type of reaction: hydrolysis versus transglucosylation
VL  - 98
IS  - 14
SP  - 6317
EP  - 6328
DO  - 10.1007/s00253-014-5587-9
ER  - 
@article{
author = "Dusan, Velickovic and Nenad, Milosavic and Dejan, Bezbradica and Bihelović, Filip and Segal, Ann Marie and Šegan, Dejan M. and Trbojević-Ivić, Jovana and Aleksandra, Dimitrijevic",
year = "2014",
abstract = "Our investigation of the catalytic properties of Saccharomyces cerevisiae alpha-glucosidase (AGL) using hydroxybenzyl alcohol (HBA) isomers as transglucosylation substrates and their glucosides in hydrolytic reactions demonstrated interesting findings pertaining to the aglycon specificity of this important enzyme. AGL specificity increased from the para(p)- to the ortho(o)-HBA isomer in transglucosylation, whereas such AGL aglycon specificity was not seen in hydrolysis, thus indicating that the second step of the reaction (i.e., binding of the glucosyl acceptor) is rate-determining. To study the influence of substitution pattern on AGL kinetics, we compared AGL specificity, inferred from kinetic constants, for HBA isomers and other aglycon substrates. The demonstrated inhibitory effects of HBA isomers and their corresponding glucosides on AGL-catalyzed hydrolysis of p-nitrophenyl a-glucoside (PNPG) suggest that HBA glucosides act as competitive, whereas HBA isomers are noncompetitive, inhibitors. As such, we postulate that aromatic moieties cannot bind to an active site unless an enzyme-glucosyl complex has already formed, but they can interact with other regions of the enzyme molecule resulting in inhibition.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "The specificity of alpha-glucosidase from Saccharomyces cerevisiae differs depending on the type of reaction: hydrolysis versus transglucosylation",
volume = "98",
number = "14",
pages = "6317-6328",
doi = "10.1007/s00253-014-5587-9"
}
Dusan, V., Nenad, M., Dejan, B., Bihelović, F., Segal, A. M., Šegan, D. M., Trbojević-Ivić, J.,& Aleksandra, D.. (2014). The specificity of alpha-glucosidase from Saccharomyces cerevisiae differs depending on the type of reaction: hydrolysis versus transglucosylation. in Applied Microbiology and Biotechnology
Springer, New York., 98(14), 6317-6328.
https://doi.org/10.1007/s00253-014-5587-9
Dusan V, Nenad M, Dejan B, Bihelović F, Segal AM, Šegan DM, Trbojević-Ivić J, Aleksandra D. The specificity of alpha-glucosidase from Saccharomyces cerevisiae differs depending on the type of reaction: hydrolysis versus transglucosylation. in Applied Microbiology and Biotechnology. 2014;98(14):6317-6328.
doi:10.1007/s00253-014-5587-9 .
Dusan, Velickovic, Nenad, Milosavic, Dejan, Bezbradica, Bihelović, Filip, Segal, Ann Marie, Šegan, Dejan M., Trbojević-Ivić, Jovana, Aleksandra, Dimitrijevic, "The specificity of alpha-glucosidase from Saccharomyces cerevisiae differs depending on the type of reaction: hydrolysis versus transglucosylation" in Applied Microbiology and Biotechnology, 98, no. 14 (2014):6317-6328,
https://doi.org/10.1007/s00253-014-5587-9 . .
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