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 . .

TY  - THES
AU  - Trajković, Miloš D.
PY  - 2015
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=3181
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:11541/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=47673103
UR  - http://nardus.mpn.gov.rs/123456789/5892
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/2677
AB  - Razvijene su dve enantioselektivne formalne sinteze oseltamivir-fosfata i totalnaenantioselektivna sinteza svainsonina. U prvoj sintezi oseltamivir-fosfata kao ključnereakcije korišćene su enantioselektivna aldolna adicija hiralnog borovog enolata nahiralni aldehid, čime su formirana dva nova stereocentra i aldolna kondenzacija kojomje nagrađen cikloheksenski prsten. U drugoj sintezi oseltamivir-fosfata kao ključnereakcije korišćene su alilovanje hiralnog aldehida u vodenim uslovima i ciklizacionametateza za formiranje cikloheksenskog skeleta. Na osnovu rezultata do kojih se došlo usintezi oseltamivira, razvijena je enantioselektivna sinteza Garner-ovog aldehida, kojase zasniva na transfer-hidrogenolizi odgovarajućeg tioestra. Totalna enantioselektivnasinteza svainsonina počiva na taktičkoj kombinaciji organokatalizovane aldolne adicije ireduktivnog aminovanja, čime se formira pirolidinski skelet sa tri definisanastereocentra, dok je piperidinski prsten zatvoren primenom još jedne reakcijereduktivnog aminovanja. U okviru sintetičke studije platenzimicina ostvaren je prodorprema formalnoj sintezi oksatetracikličnog Nicolaou-ovog intermedijera, gde je uspešnonapravljen spiro-biciklični intermedijer. Kao ključne reakcije za sintezu ovog jedinjenjaiskorišćene su Mukaiyama–Michael-ova reakcija, praćena 6–endo-trig ciklizacijom,dekarboksilativno alilovanje i ciklizaciona metateza.
AB  - Two enantioselective formal syntheses of oseltamivir phosphate and theenantioselective total synthesis of swainsonine have been accomplished. The keyreactions in the first synthesis of oseltamivir phosphate were enantioselective aldoladditions of boron enolate to chiral aldehyde, that formed two new stereocenters, andaldol condensation for the construction of cyclohexene ring. In the second synthesis ofoseltamivir phosphate, the pivotal steps were allylation of chiral aldehydes underaqueous conditions and ring closing metathesis for the formation of cyclohexene ring.Based on the results for the first synthesis of oseltamivir, a new enantioselectivesynthesis of Garner aldehyde was developed, that hinges on the transfer hydrogenationof the corresponding thioester. Total enantioselective synthesis of swinsonine was basedon the tactical combination of organocatalyzed aldol addition and reductive aminationfor the formation of the pyrrolidine skeleton with three contiguous stereocenter,followed by the piperidine ring formation by a second reductive amination. Within asynthetic study on platensimycin, a breakthrough towards formal synthesis ofoxatetracyclic Nicolaou's intermediate was achieved, by successfully synthesizing thespirobicyclic intermediate. The key steps in the synthesis of this compound wereMukaiyama-Michael's reaction followed by 6-endo-trig cyclisation, decarboxylativeallylation and ring closing metathesis.
PB  - Универзитет у Београду, Хемијски факултет
T2  - Универзитет у Београду
T1  - Enantioselektivne sinteze jedinjenja značajnih za medicinu: oseltamivir-fosfat (tamifly), svainsonin i platenzimicin
T1  - oseltamivir phosphate (tamiflu), swainsonine and platensimycin
UR  - https://hdl.handle.net/21.15107/rcub_nardus_5892
ER  - 

@phdthesis{
author = "Trajković, Miloš D.",
year = "2015",
abstract = "Razvijene su dve enantioselektivne formalne sinteze oseltamivir-fosfata i totalnaenantioselektivna sinteza svainsonina. U prvoj sintezi oseltamivir-fosfata kao ključnereakcije korišćene su enantioselektivna aldolna adicija hiralnog borovog enolata nahiralni aldehid, čime su formirana dva nova stereocentra i aldolna kondenzacija kojomje nagrađen cikloheksenski prsten. U drugoj sintezi oseltamivir-fosfata kao ključnereakcije korišćene su alilovanje hiralnog aldehida u vodenim uslovima i ciklizacionametateza za formiranje cikloheksenskog skeleta. Na osnovu rezultata do kojih se došlo usintezi oseltamivira, razvijena je enantioselektivna sinteza Garner-ovog aldehida, kojase zasniva na transfer-hidrogenolizi odgovarajućeg tioestra. Totalna enantioselektivnasinteza svainsonina počiva na taktičkoj kombinaciji organokatalizovane aldolne adicije ireduktivnog aminovanja, čime se formira pirolidinski skelet sa tri definisanastereocentra, dok je piperidinski prsten zatvoren primenom još jedne reakcijereduktivnog aminovanja. U okviru sintetičke studije platenzimicina ostvaren je prodorprema formalnoj sintezi oksatetracikličnog Nicolaou-ovog intermedijera, gde je uspešnonapravljen spiro-biciklični intermedijer. Kao ključne reakcije za sintezu ovog jedinjenjaiskorišćene su Mukaiyama–Michael-ova reakcija, praćena 6–endo-trig ciklizacijom,dekarboksilativno alilovanje i ciklizaciona metateza., Two enantioselective formal syntheses of oseltamivir phosphate and theenantioselective total synthesis of swainsonine have been accomplished. The keyreactions in the first synthesis of oseltamivir phosphate were enantioselective aldoladditions of boron enolate to chiral aldehyde, that formed two new stereocenters, andaldol condensation for the construction of cyclohexene ring. In the second synthesis ofoseltamivir phosphate, the pivotal steps were allylation of chiral aldehydes underaqueous conditions and ring closing metathesis for the formation of cyclohexene ring.Based on the results for the first synthesis of oseltamivir, a new enantioselectivesynthesis of Garner aldehyde was developed, that hinges on the transfer hydrogenationof the corresponding thioester. Total enantioselective synthesis of swinsonine was basedon the tactical combination of organocatalyzed aldol addition and reductive aminationfor the formation of the pyrrolidine skeleton with three contiguous stereocenter,followed by the piperidine ring formation by a second reductive amination. Within asynthetic study on platensimycin, a breakthrough towards formal synthesis ofoxatetracyclic Nicolaou's intermediate was achieved, by successfully synthesizing thespirobicyclic intermediate. The key steps in the synthesis of this compound wereMukaiyama-Michael's reaction followed by 6-endo-trig cyclisation, decarboxylativeallylation and ring closing metathesis.",
publisher = "Универзитет у Београду, Хемијски факултет",
journal = "Универзитет у Београду",
title = "Enantioselektivne sinteze jedinjenja značajnih za medicinu: oseltamivir-fosfat (tamifly), svainsonin i platenzimicin, oseltamivir phosphate (tamiflu), swainsonine and platensimycin",
url = "https://hdl.handle.net/21.15107/rcub_nardus_5892"
}

Trajković, M. D.. (2015). Enantioselektivne sinteze jedinjenja značajnih za medicinu: oseltamivir-fosfat (tamifly), svainsonin i platenzimicin. in Универзитет у Београду
Универзитет у Београду, Хемијски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_5892

Trajković MD. Enantioselektivne sinteze jedinjenja značajnih za medicinu: oseltamivir-fosfat (tamifly), svainsonin i platenzimicin. in Универзитет у Београду. 2015;.
https://hdl.handle.net/21.15107/rcub_nardus_5892 .

Trajković, Miloš D., "Enantioselektivne sinteze jedinjenja značajnih za medicinu: oseltamivir-fosfat (tamifly), svainsonin i platenzimicin" in Универзитет у Београду (2015),
https://hdl.handle.net/21.15107/rcub_nardus_5892 .