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Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach

Stereoselektivne sinteze α-hidroksi-β-aminokiselina iz prirodnih hiralnih prekursora

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2004
546.pdf (148.5Kb)
Authors
Tasić, Gordana
Matović, Radomir
Saičić, Radomir N.
Article (Published version)
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Abstract
A method for the stereoselective homologation of -amino acids into syn-α-hydroxy-β-amino acids is described, based on the conversion of stereoisomeric cyanohydrins into trans-oxazolines. The synthetic potential of the method is illustrated in the enantioselective formal synthesis of Bestatin.
Opisana je metoda za stereoselektivnu sintezu α-hidroksi-β-aminokiselina syn-konfiguracije, polazeći od α-aminokiselina, kao prirodnih hiralnih prekursora. Enantioselektivnost procesa zavisi od strukture polazne aminokiseline, kao i reakcionih uslova. Primena ove metode ilustrovana je u sintezi (2S,3R)-3-amino-2-hidroksi-4-fenilbutanske kiseline, konstituenta nekoliko važnih biološki aktivnih jedinjenja.
Keywords:
amino acids / cyanohydrins / bestatin / AHPA / oxazoline
Source:
Journal of the Serbian Chemical Society, 2004, 69, 11, 981-990
Publisher:
  • Srpsko hemijsko društvo, Beograd

DOI: 10.2298/JSC0411981T

ISSN: 0352-5139

WoS: 000226120300018

Scopus: 2-s2.0-24944448953
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9
8
URI
https://farfar.pharmacy.bg.ac.rs/handle/123456789/548
Collections
  • Radovi istraživača / Researchers’ publications
Institution/Community
Pharmacy
TY  - JOUR
AU  - Tasić, Gordana
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2004
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/548
AB  - A method for the stereoselective homologation of -amino acids into syn-α-hydroxy-β-amino acids is described, based on the conversion of stereoisomeric cyanohydrins into trans-oxazolines. The synthetic potential of the method is illustrated in the enantioselective formal synthesis of Bestatin.
AB  - Opisana je metoda za stereoselektivnu sintezu α-hidroksi-β-aminokiselina syn-konfiguracije, polazeći od α-aminokiselina, kao prirodnih hiralnih prekursora. Enantioselektivnost procesa zavisi od strukture polazne aminokiseline, kao i reakcionih uslova. Primena ove metode ilustrovana je u sintezi (2S,3R)-3-amino-2-hidroksi-4-fenilbutanske kiseline, konstituenta nekoliko važnih biološki aktivnih jedinjenja.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach
T1  - Stereoselektivne sinteze α-hidroksi-β-aminokiselina iz prirodnih hiralnih prekursora
VL  - 69
IS  - 11
SP  - 981
EP  - 990
DO  - 10.2298/JSC0411981T
ER  - 
@article{
author = "Tasić, Gordana and Matović, Radomir and Saičić, Radomir N.",
year = "2004",
abstract = "A method for the stereoselective homologation of -amino acids into syn-α-hydroxy-β-amino acids is described, based on the conversion of stereoisomeric cyanohydrins into trans-oxazolines. The synthetic potential of the method is illustrated in the enantioselective formal synthesis of Bestatin., Opisana je metoda za stereoselektivnu sintezu α-hidroksi-β-aminokiselina syn-konfiguracije, polazeći od α-aminokiselina, kao prirodnih hiralnih prekursora. Enantioselektivnost procesa zavisi od strukture polazne aminokiseline, kao i reakcionih uslova. Primena ove metode ilustrovana je u sintezi (2S,3R)-3-amino-2-hidroksi-4-fenilbutanske kiseline, konstituenta nekoliko važnih biološki aktivnih jedinjenja.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach, Stereoselektivne sinteze α-hidroksi-β-aminokiselina iz prirodnih hiralnih prekursora",
volume = "69",
number = "11",
pages = "981-990",
doi = "10.2298/JSC0411981T"
}
Tasić, G., Matović, R.,& Saičić, R. N.. (2004). Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 69(11), 981-990.
https://doi.org/10.2298/JSC0411981T
Tasić G, Matović R, Saičić RN. Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach. in Journal of the Serbian Chemical Society. 2004;69(11):981-990.
doi:10.2298/JSC0411981T .
Tasić, Gordana, Matović, Radomir, Saičić, Radomir N., "Stereoselective synthesis of α-hydroxy-β-amino acids: The chiral pool approach" in Journal of the Serbian Chemical Society, 69, no. 11 (2004):981-990,
https://doi.org/10.2298/JSC0411981T . .

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