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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
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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:
  • Serbian Chemical Society

DOI: 10.2298/JSC0411981T

ISSN: 0352-5139

WoS: 000226120300018

Scopus: 2-s2.0-24944448953
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URI
http://cer.ihtm.bg.ac.rs/handle/123456789/142
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