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

A method for the stereoselective homologation of ?-amino acids into syn-?-hydroxy-?-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. Opisa...

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Bibliographic Details
Published inJournal of the Serbian Chemical Society Vol. 69; no. 11; pp. 981 - 990
Main Authors Tasic, Gordana, Matovic, Radomir, Saicic, Radomir
Format Journal Article
LanguageEnglish
Published Serbian Chemical Society 2004
Subjects
ahpa
amino acids
bestatin
cyanohydrins
oxazoline
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Summary:A method for the stereoselective homologation of ?-amino acids into syn-?-hydroxy-?-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 ?-hidroksi-?-aminokiselina syn-konfiguracije, polazeci od ?-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 vaznih bioloski aktivnih jedinjenja.
ISSN:0352-5139
1820-7421
DOI:10.2298/JSC0411981T