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.
TY - JOUR
AU - Tasić, Gordana
AU - Matović, Radomir
AU - Saičić, Radomir N.
PY - 2004
UR - https://cer.ihtm.bg.ac.rs/handle/123456789/142
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 - Serbian Chemical Society
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 = "Serbian Chemical Society",
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
Serbian Chemical Society., 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 . .
