Marjanović-Trajković, Jasna

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orcid::0000-0002-3966-6120
  • Marjanović-Trajković, Jasna (11)
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Author's Bibliography

Primena taktičke kombinacije organokatalitičke aldolizacije i reduktivnog aminovanja na sintezu polihidroksilovanih alkaloida značajnih za medicinu

Marjanović-Trajković, Jasna

(Универзитет у Београду, Хемијски факултет, 2018)

TY  - THES
AU  - Marjanović-Trajković, Jasna
PY  - 2018
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=5734
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:17557/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=50004495
UR  - http://nardus.mpn.gov.rs/123456789/9408
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2764
AB  - Ispitana je dvostruka asimetrična indukcija u aldolnim reakcijama između dioksanona ihiralnih acikličnih α-supstituisanih aldehida katalizovanih prolinom, i tom prilikom jeutvrđeno da je stereohemijski ishod ove reakcije kontrolisan reagensom, sa dobrimstepenom dijastereoselektivnosti. Sa cikličnim aldehidima stereokontrola nijezadovoljavajuća.Takođe, kombinacijom organokatalizovane aldolizacije i reduktivnog aminovanja,sintetisano je šest biološki aktivnih jedinjenja: (+)-2-epi-hiacintacin A2, (–)-3-epihiacintacinA1, 1-deoksi-galaktonodžirimicin (DGJ), 2,5-dideoksi-2,5-imino-D-altritol(DIA), (–)-4-epi-fagomin i (+)-aza-galaktofagomin. Pored ovih iminošećera, istimpristupom sintetisano je još tri molekula - pipekolinska kiselina, 3-hidroksipipekolinskakiselina i 4-deoksifagomin - koji predstavljaju sintetički značajne intermedijere zadobijanje drugih biološki aktivnih jedinjenja. U svim sintezama kao ključna reakcijakorišćena je asimetrična aldolna adicija 2,2-dimetil-1,3-dioksan-5-ona (dioksanona) naodgovarajući aldehid katalizovana prolinom i praćena reduktivnim aminovanjem.Formirana su dva nova stereocentra primenom principa katalitičke asimetrične sinteze ijedan dijastereoselektivnim reduktivnim aminovanjem.
AB  - Double asymmetric induction was investigated in proline-catalyzed aldol additionsbetween dioxanone and chiral α-substituted aldehydes, and it was found that, withacyclic aldehydes, the stereochemical outcome of this reaction was controlled by areagent, with a good level of diastereoselectivity. Stereocontrol with cyclic aldehydes isnot satisfactory.Six biologically active compounds as well as some significantly useful intermediateswere synthesized by a combination of organocatalytic aldol addition and reductiveamination: (+)-2-epi-hyacinthacine A2, (–)-3-epi-hyacinthacine A1, 1-deoxygalactonojirimycin(DGJ), 2,5-dideoxy-2,5-imino-D-altritol (DIA), (–)-4-epi-fagomine and (+)-aza-galacto-fagomine. In addition to these iminosugars, three other molecules -pipecolic acid, 3-hydroxypipecolic acid and 4-deoxyfagomine - are synthesized byapplying this tactical combination on the same way, and they are significantintermediates in synthesis of other biologically active compounds. Proline-catalyzedasymmetric aldol addition of 2,2-dimethyl-1,3-dioxan-5-one (dioxanone) to thecorresponding aldehyde, followed by reductive amination, was used as the keytransformation in all syntheses. Two new stereocentres were formed in these reactionsusing the principle of catalytic asymmetric synthesis and one by diastereoselectivereductive amination.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Primena taktičke kombinacije organokatalitičke aldolizacije i reduktivnog aminovanja na sintezu polihidroksilovanih alkaloida značajnih za medicinu
UR  - https://hdl.handle.net/21.15107/rcub_nardus_9408
ER  - 
@phdthesis{
author = "Marjanović-Trajković, Jasna",
year = "2018",
abstract = "Ispitana je dvostruka asimetrična indukcija u aldolnim reakcijama između dioksanona ihiralnih acikličnih α-supstituisanih aldehida katalizovanih prolinom, i tom prilikom jeutvrđeno da je stereohemijski ishod ove reakcije kontrolisan reagensom, sa dobrimstepenom dijastereoselektivnosti. Sa cikličnim aldehidima stereokontrola nijezadovoljavajuća.Takođe, kombinacijom organokatalizovane aldolizacije i reduktivnog aminovanja,sintetisano je šest biološki aktivnih jedinjenja: (+)-2-epi-hiacintacin A2, (–)-3-epihiacintacinA1, 1-deoksi-galaktonodžirimicin (DGJ), 2,5-dideoksi-2,5-imino-D-altritol(DIA), (–)-4-epi-fagomin i (+)-aza-galaktofagomin. Pored ovih iminošećera, istimpristupom sintetisano je još tri molekula - pipekolinska kiselina, 3-hidroksipipekolinskakiselina i 4-deoksifagomin - koji predstavljaju sintetički značajne intermedijere zadobijanje drugih biološki aktivnih jedinjenja. U svim sintezama kao ključna reakcijakorišćena je asimetrična aldolna adicija 2,2-dimetil-1,3-dioksan-5-ona (dioksanona) naodgovarajući aldehid katalizovana prolinom i praćena reduktivnim aminovanjem.Formirana su dva nova stereocentra primenom principa katalitičke asimetrične sinteze ijedan dijastereoselektivnim reduktivnim aminovanjem., Double asymmetric induction was investigated in proline-catalyzed aldol additionsbetween dioxanone and chiral α-substituted aldehydes, and it was found that, withacyclic aldehydes, the stereochemical outcome of this reaction was controlled by areagent, with a good level of diastereoselectivity. Stereocontrol with cyclic aldehydes isnot satisfactory.Six biologically active compounds as well as some significantly useful intermediateswere synthesized by a combination of organocatalytic aldol addition and reductiveamination: (+)-2-epi-hyacinthacine A2, (–)-3-epi-hyacinthacine A1, 1-deoxygalactonojirimycin(DGJ), 2,5-dideoxy-2,5-imino-D-altritol (DIA), (–)-4-epi-fagomine and (+)-aza-galacto-fagomine. In addition to these iminosugars, three other molecules -pipecolic acid, 3-hydroxypipecolic acid and 4-deoxyfagomine - are synthesized byapplying this tactical combination on the same way, and they are significantintermediates in synthesis of other biologically active compounds. Proline-catalyzedasymmetric aldol addition of 2,2-dimethyl-1,3-dioxan-5-one (dioxanone) to thecorresponding aldehyde, followed by reductive amination, was used as the keytransformation in all syntheses. Two new stereocentres were formed in these reactionsusing the principle of catalytic asymmetric synthesis and one by diastereoselectivereductive amination.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Primena taktičke kombinacije organokatalitičke aldolizacije i reduktivnog aminovanja na sintezu polihidroksilovanih alkaloida značajnih za medicinu",
url = "https://hdl.handle.net/21.15107/rcub_nardus_9408"
}
Marjanović-Trajković, J.. (2018). Primena taktičke kombinacije organokatalitičke aldolizacije i reduktivnog aminovanja na sintezu polihidroksilovanih alkaloida značajnih za medicinu. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_9408
Marjanović-Trajković J. Primena taktičke kombinacije organokatalitičke aldolizacije i reduktivnog aminovanja na sintezu polihidroksilovanih alkaloida značajnih za medicinu. in Универзитет у Београду. 2018;.
https://hdl.handle.net/21.15107/rcub_nardus_9408 .
Marjanović-Trajković, Jasna, "Primena taktičke kombinacije organokatalitičke aldolizacije i reduktivnog aminovanja na sintezu polihidroksilovanih alkaloida značajnih za medicinu" in Универзитет у Београду (2018),
https://hdl.handle.net/21.15107/rcub_nardus_9408 .

A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)

Marjanović-Trajković, Jasna; Ferjančić, Zorana; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2017)

TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3025
AB  - A catalytic asymmetric synthesis of (+)-aza-galacto-fagomine (AGF) - the most promising compound for the pharmacological chaperone therapy of Krabbe disease was accomplished in six steps, in 14% overall yield. The synthesis hinges on the combination of organocatalyzed aldolization and reductive hydrazination.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)
VL  - 73
IS  - 18
SP  - 2630
DO  - 10.1016/j.tet.2017.03.052
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir",
year = "2017",
abstract = "A catalytic asymmetric synthesis of (+)-aza-galacto-fagomine (AGF) - the most promising compound for the pharmacological chaperone therapy of Krabbe disease was accomplished in six steps, in 14% overall yield. The synthesis hinges on the combination of organocatalyzed aldolization and reductive hydrazination.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)",
volume = "73",
number = "18",
pages = "2630",
doi = "10.1016/j.tet.2017.03.052"
}
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2017). A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF). in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 73(18), 2630.
https://doi.org/10.1016/j.tet.2017.03.052
Marjanović-Trajković J, Ferjančić Z, Saičić R. A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF). in Tetrahedron. 2017;73(18):2630.
doi:10.1016/j.tet.2017.03.052 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)" in Tetrahedron, 73, no. 18 (2017):2630,
https://doi.org/10.1016/j.tet.2017.03.052 . .
3
2
5
2

Supplementary data for article: Marjanović-Trajković, J.; Ferjančić, Z.; Saičić, R. A Short Stereoselective Synthesis of (+)-Aza-Galacto-Fagomine (AGF). Tetrahedron 2017, 73 (18), 2630. https://doi.org/10.1016/j.tet.2017.03.052

Marjanović-Trajković, Jasna; Ferjančić, Zorana; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2017)

TY  - DATA
AU  - Marjanović-Trajković, Jasna
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3026
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Supplementary data for article: Marjanović-Trajković, J.; Ferjančić, Z.; Saičić, R. A Short Stereoselective Synthesis of (+)-Aza-Galacto-Fagomine (AGF). Tetrahedron 2017, 73 (18), 2630. https://doi.org/10.1016/j.tet.2017.03.052
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3026
ER  - 
@misc{
author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir",
year = "2017",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Supplementary data for article: Marjanović-Trajković, J.; Ferjančić, Z.; Saičić, R. A Short Stereoselective Synthesis of (+)-Aza-Galacto-Fagomine (AGF). Tetrahedron 2017, 73 (18), 2630. https://doi.org/10.1016/j.tet.2017.03.052",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3026"
}
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2017). Supplementary data for article: Marjanović-Trajković, J.; Ferjančić, Z.; Saičić, R. A Short Stereoselective Synthesis of (+)-Aza-Galacto-Fagomine (AGF). Tetrahedron 2017, 73 (18), 2630. https://doi.org/10.1016/j.tet.2017.03.052. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3026
Marjanović-Trajković J, Ferjančić Z, Saičić R. Supplementary data for article: Marjanović-Trajković, J.; Ferjančić, Z.; Saičić, R. A Short Stereoselective Synthesis of (+)-Aza-Galacto-Fagomine (AGF). Tetrahedron 2017, 73 (18), 2630. https://doi.org/10.1016/j.tet.2017.03.052. in Tetrahedron. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3026 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "Supplementary data for article: Marjanović-Trajković, J.; Ferjančić, Z.; Saičić, R. A Short Stereoselective Synthesis of (+)-Aza-Galacto-Fagomine (AGF). Tetrahedron 2017, 73 (18), 2630. https://doi.org/10.1016/j.tet.2017.03.052" in Tetrahedron (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3026 .

Supplementary data for the article: Marjanovic Trajkovic, J.; Milanovic, V.; Ferjancic, Z.; Saicic, R. N. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-Dioxane-5-One to Acyclic Chiral α-Branched Aldehydes. European Journal of Organic Chemistry 2017, 2017 (41), 6146–6153. https://doi.org/10.1002/ejoc.201701073

Marjanović-Trajković, Jasna; Milanović, Vesna D.; Ferjančić, Zorana; Saičić, Radomir

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

TY  - DATA
AU  - Marjanović-Trajković, Jasna
AU  - Milanović, Vesna D.
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3229
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Supplementary data for the article: Marjanovic Trajkovic, J.; Milanovic, V.; Ferjancic, Z.; Saicic, R. N. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-Dioxane-5-One to Acyclic Chiral α-Branched Aldehydes. European Journal of Organic Chemistry 2017, 2017 (41), 6146–6153. https://doi.org/10.1002/ejoc.201701073
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3229
ER  - 
@misc{
author = "Marjanović-Trajković, Jasna and Milanović, Vesna D. and Ferjančić, Zorana and Saičić, Radomir",
year = "2017",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Supplementary data for the article: Marjanovic Trajkovic, J.; Milanovic, V.; Ferjancic, Z.; Saicic, R. N. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-Dioxane-5-One to Acyclic Chiral α-Branched Aldehydes. European Journal of Organic Chemistry 2017, 2017 (41), 6146–6153. https://doi.org/10.1002/ejoc.201701073",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3229"
}
Marjanović-Trajković, J., Milanović, V. D., Ferjančić, Z.,& Saičić, R.. (2017). Supplementary data for the article: Marjanovic Trajkovic, J.; Milanovic, V.; Ferjancic, Z.; Saicic, R. N. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-Dioxane-5-One to Acyclic Chiral α-Branched Aldehydes. European Journal of Organic Chemistry 2017, 2017 (41), 6146–6153. https://doi.org/10.1002/ejoc.201701073. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3229
Marjanović-Trajković J, Milanović VD, Ferjančić Z, Saičić R. Supplementary data for the article: Marjanovic Trajkovic, J.; Milanovic, V.; Ferjancic, Z.; Saicic, R. N. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-Dioxane-5-One to Acyclic Chiral α-Branched Aldehydes. European Journal of Organic Chemistry 2017, 2017 (41), 6146–6153. https://doi.org/10.1002/ejoc.201701073. in European Journal of Organic Chemistry. 2017;.
https://hdl.handle.net/21.15107/rcub_cherry_3229 .
Marjanović-Trajković, Jasna, Milanović, Vesna D., Ferjančić, Zorana, Saičić, Radomir, "Supplementary data for the article: Marjanovic Trajkovic, J.; Milanovic, V.; Ferjancic, Z.; Saicic, R. N. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-Dioxane-5-One to Acyclic Chiral α-Branched Aldehydes. European Journal of Organic Chemistry 2017, 2017 (41), 6146–6153. https://doi.org/10.1002/ejoc.201701073" in European Journal of Organic Chemistry (2017),
https://hdl.handle.net/21.15107/rcub_cherry_3229 .

On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes

Marjanović-Trajković, Jasna; Milanović, Vesna D.; Ferjančić, Zorana; Saičić, Radomir

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

TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Milanović, Vesna D.
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2410
AB  - Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes
IS  - 41
SP  - 6146
EP  - 6153
DO  - 10.1002/ejoc.201701073
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Milanović, Vesna D. and Ferjančić, Zorana and Saičić, Radomir",
year = "2017",
abstract = "Reagent stereocontrol in the proline-catalyzed aldol reaction of 2,2-dimethyl-1,3-dioxane-5-one 1 with chiral aldehydes has been investigated. Synthetically useful levels of diastereoselectivity could be achieved in reactions with acyclic chiral alpha-oxy and alpha-amino aldehydes in both matched and mismatched cases. By using this reaction as a key step, two medicinally relevant azasugars, 1-deoxy-galactonojirimycin (9) and 2,5-dideoxy-2,5-imino-d-altritol (10), were efficiently synthesized.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes",
number = "41",
pages = "6146-6153",
doi = "10.1002/ejoc.201701073"
}
Marjanović-Trajković, J., Milanović, V. D., Ferjančić, Z.,& Saičić, R.. (2017). On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim.(41), 6146-6153.
https://doi.org/10.1002/ejoc.201701073
Marjanović-Trajković J, Milanović VD, Ferjančić Z, Saičić R. On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes. in European Journal of Organic Chemistry. 2017;(41):6146-6153.
doi:10.1002/ejoc.201701073 .
Marjanović-Trajković, Jasna, Milanović, Vesna D., Ferjančić, Zorana, Saičić, Radomir, "On the Asymmetric Induction in Proline-Catalyzed Aldol Reactions: Reagent-Controlled Addition Reactions of 2,2-Dimethyl-1,3-dioxane-5-one to Acyclic Chiral alpha-Branched Aldehydes" in European Journal of Organic Chemistry, no. 41 (2017):6146-6153,
https://doi.org/10.1002/ejoc.201701073 . .
1
9
5
9
8

A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)

Marjanović-Trajković, Jasna; Ferjančić, Zorana; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2017)

TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2017
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2452
AB  - A catalytic asymmetric synthesis of (+)-aza-galacto-fagomine (AGF) - the most promising compound for the pharmacological chaperone therapy of Krabbe disease was accomplished in six steps, in 14% overall yield. The synthesis hinges on the combination of organocatalyzed aldolization and reductive hydrazination.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)
VL  - 73
IS  - 18
SP  - 2630
DO  - 10.1016/j.tet.2017.03.052
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir",
year = "2017",
abstract = "A catalytic asymmetric synthesis of (+)-aza-galacto-fagomine (AGF) - the most promising compound for the pharmacological chaperone therapy of Krabbe disease was accomplished in six steps, in 14% overall yield. The synthesis hinges on the combination of organocatalyzed aldolization and reductive hydrazination.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)",
volume = "73",
number = "18",
pages = "2630",
doi = "10.1016/j.tet.2017.03.052"
}
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2017). A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF). in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 73(18), 2630.
https://doi.org/10.1016/j.tet.2017.03.052
Marjanović-Trajković J, Ferjančić Z, Saičić R. A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF). in Tetrahedron. 2017;73(18):2630.
doi:10.1016/j.tet.2017.03.052 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "A short stereoselective synthesis of (+)-aza-galacto-fagomine (AGF)" in Tetrahedron, 73, no. 18 (2017):2630,
https://doi.org/10.1016/j.tet.2017.03.052 . .
3
2
5
2

Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids

Marjanović-Trajković, Jasna; Ferjančić, Zorana; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2015)

TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3389
AB  - The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids
VL  - 71
IS  - 38
SP  - 6784
EP  - 6789
DO  - 10.1016/j.tet.2015.07.036
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir",
year = "2015",
abstract = "The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids",
volume = "71",
number = "38",
pages = "6784-6789",
doi = "10.1016/j.tet.2015.07.036"
}
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2015). Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 71(38), 6784-6789.
https://doi.org/10.1016/j.tet.2015.07.036
Marjanović-Trajković J, Ferjančić Z, Saičić R. Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids. in Tetrahedron. 2015;71(38):6784-6789.
doi:10.1016/j.tet.2015.07.036 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids" in Tetrahedron, 71, no. 38 (2015):6784-6789,
https://doi.org/10.1016/j.tet.2015.07.036 . .
1
8
7
10
7

Supplementary data for article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. https://doi.org/10.1016/j.tet.2015.07.036

Marjanović-Trajković, Jasna; Ferjančić, Zorana; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2015)

TY  - DATA
AU  - Marjanović-Trajković, Jasna
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3390
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Supplementary data for article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. https://doi.org/10.1016/j.tet.2015.07.036
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3390
ER  - 
@misc{
author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir",
year = "2015",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Supplementary data for article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. https://doi.org/10.1016/j.tet.2015.07.036",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3390"
}
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2015). Supplementary data for article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. https://doi.org/10.1016/j.tet.2015.07.036. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford..
https://hdl.handle.net/21.15107/rcub_cherry_3390
Marjanović-Trajković J, Ferjančić Z, Saičić R. Supplementary data for article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. https://doi.org/10.1016/j.tet.2015.07.036. in Tetrahedron. 2015;.
https://hdl.handle.net/21.15107/rcub_cherry_3390 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "Supplementary data for article: Marjanovic, J.; Ferjancic, Z.; Saicic, R. N. Organocatalyzed Synthesis of (-)-4-Epi-Fagomine and the Corresponding Pipecolic Acids. Tetrahedron 2015, 71 (38), 6784–6789. https://doi.org/10.1016/j.tet.2015.07.036" in Tetrahedron (2015),
https://hdl.handle.net/21.15107/rcub_cherry_3390 .

Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids

Marjanović-Trajković, Jasna; Ferjančić, Zorana; Saičić, Radomir

(Pergamon-Elsevier Science Ltd, Oxford, 2015)

TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2015
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1951
AB  - The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Tetrahedron
T1  - Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids
VL  - 71
IS  - 38
SP  - 6784
EP  - 6789
DO  - 10.1016/j.tet.2015.07.036
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Ferjančić, Zorana and Saičić, Radomir",
year = "2015",
abstract = "The enantioselective synthesis of 4-epi-fagomine was accomplished starting from dioxanone and Cbz-protected benyzlamine, in 4 steps, with 18% overall yield. The key feature of this synthetic approach is the tactical combination of reactions: organocatalyzed aldolization/reductive amination, which allows for a quick formation of heterocyclic rings with defined absolute configuration of all stereogenic centers. Two hydroxypipecolic acids and a reduced fagomine analogue were also synthesized.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Tetrahedron",
title = "Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids",
volume = "71",
number = "38",
pages = "6784-6789",
doi = "10.1016/j.tet.2015.07.036"
}
Marjanović-Trajković, J., Ferjančić, Z.,& Saičić, R.. (2015). Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids. in Tetrahedron
Pergamon-Elsevier Science Ltd, Oxford., 71(38), 6784-6789.
https://doi.org/10.1016/j.tet.2015.07.036
Marjanović-Trajković J, Ferjančić Z, Saičić R. Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids. in Tetrahedron. 2015;71(38):6784-6789.
doi:10.1016/j.tet.2015.07.036 .
Marjanović-Trajković, Jasna, Ferjančić, Zorana, Saičić, Radomir, "Organocatalyzed synthesis of (-)-4-epi-fagomine and the corresponding pipecolic acids" in Tetrahedron, 71, no. 38 (2015):6784-6789,
https://doi.org/10.1016/j.tet.2015.07.036 . .
1
8
7
10
7

Supplementary data for article: Marjanović-Trajković, J.; Divjakovic, V.; Matovic, R.; Ferjančić, Z.; Saičić, R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-Epi-Hyacinthacine A(2) and (-)-3-Epi-Hyacinthacine A(1). European Journal of Organic Chemistry 2013, 2013 (25), 5555–5560. https://doi.org/10.1002/ejoc.201300716

Marjanović-Trajković, Jasna; Divjaković, Vladimir; Matović, Radomir; Ferjančić, Zorana; Saičić, Radomir

(Wiley-V C H Verlag Gmbh, Weinheim, 2013)

TY  - DATA
AU  - Marjanović-Trajković, Jasna
AU  - Divjaković, Vladimir
AU  - Matović, Radomir
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3489
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Supplementary data for article: Marjanović-Trajković, J.; Divjakovic, V.; Matovic, R.; Ferjančić, Z.; Saičić, R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-Epi-Hyacinthacine A(2) and (-)-3-Epi-Hyacinthacine A(1). European Journal of Organic Chemistry 2013, 2013 (25), 5555–5560. https://doi.org/10.1002/ejoc.201300716
UR  - https://hdl.handle.net/21.15107/rcub_cherry_3489
ER  - 
@misc{
author = "Marjanović-Trajković, Jasna and Divjaković, Vladimir and Matović, Radomir and Ferjančić, Zorana and Saičić, Radomir",
year = "2013",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Supplementary data for article: Marjanović-Trajković, J.; Divjakovic, V.; Matovic, R.; Ferjančić, Z.; Saičić, R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-Epi-Hyacinthacine A(2) and (-)-3-Epi-Hyacinthacine A(1). European Journal of Organic Chemistry 2013, 2013 (25), 5555–5560. https://doi.org/10.1002/ejoc.201300716",
url = "https://hdl.handle.net/21.15107/rcub_cherry_3489"
}
Marjanović-Trajković, J., Divjaković, V., Matović, R., Ferjančić, Z.,& Saičić, R.. (2013). Supplementary data for article: Marjanović-Trajković, J.; Divjakovic, V.; Matovic, R.; Ferjančić, Z.; Saičić, R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-Epi-Hyacinthacine A(2) and (-)-3-Epi-Hyacinthacine A(1). European Journal of Organic Chemistry 2013, 2013 (25), 5555–5560. https://doi.org/10.1002/ejoc.201300716. in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim..
https://hdl.handle.net/21.15107/rcub_cherry_3489
Marjanović-Trajković J, Divjaković V, Matović R, Ferjančić Z, Saičić R. Supplementary data for article: Marjanović-Trajković, J.; Divjakovic, V.; Matovic, R.; Ferjančić, Z.; Saičić, R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-Epi-Hyacinthacine A(2) and (-)-3-Epi-Hyacinthacine A(1). European Journal of Organic Chemistry 2013, 2013 (25), 5555–5560. https://doi.org/10.1002/ejoc.201300716. in European Journal of Organic Chemistry. 2013;.
https://hdl.handle.net/21.15107/rcub_cherry_3489 .
Marjanović-Trajković, Jasna, Divjaković, Vladimir, Matović, Radomir, Ferjančić, Zorana, Saičić, Radomir, "Supplementary data for article: Marjanović-Trajković, J.; Divjakovic, V.; Matovic, R.; Ferjančić, Z.; Saičić, R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-Epi-Hyacinthacine A(2) and (-)-3-Epi-Hyacinthacine A(1). European Journal of Organic Chemistry 2013, 2013 (25), 5555–5560. https://doi.org/10.1002/ejoc.201300716" in European Journal of Organic Chemistry (2013),
https://hdl.handle.net/21.15107/rcub_cherry_3489 .

Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)

Marjanović-Trajković, Jasna; Divjaković, Vladimir; Matović, Radomir; Ferjančić, Zorana; Saičić, Radomir

(Wiley-V C H Verlag Gmbh, Weinheim, 2013)

TY  - JOUR
AU  - Marjanović-Trajković, Jasna
AU  - Divjaković, Vladimir
AU  - Matović, Radomir
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir
PY  - 2013
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1389
AB  - The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)
VL  - 2013
IS  - 25
SP  - 5555
EP  - 5560
DO  - 10.1002/ejoc.201300716
ER  - 
@article{
author = "Marjanović-Trajković, Jasna and Divjaković, Vladimir and Matović, Radomir and Ferjančić, Zorana and Saičić, Radomir",
year = "2013",
abstract = "The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)",
volume = "2013",
number = "25",
pages = "5555-5560",
doi = "10.1002/ejoc.201300716"
}
Marjanović-Trajković, J., Divjaković, V., Matović, R., Ferjančić, Z.,& Saičić, R.. (2013). Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim., 2013(25), 5555-5560.
https://doi.org/10.1002/ejoc.201300716
Marjanović-Trajković J, Divjaković V, Matović R, Ferjančić Z, Saičić R. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry. 2013;2013(25):5555-5560.
doi:10.1002/ejoc.201300716 .
Marjanović-Trajković, Jasna, Divjaković, Vladimir, Matović, Radomir, Ferjančić, Zorana, Saičić, Radomir, "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)" in European Journal of Organic Chemistry, 2013, no. 25 (2013):5555-5560,
https://doi.org/10.1002/ejoc.201300716 . .
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