PREPARATION OF CHIRAL SYNTHON FOR HIV PROTEASE INHIBITOR - STEREOSELECTIVE MICROBIAL REDUCTION OF N-PROTECTED ALPHA-AMINOCHLOROKETONE

Authors
PATEL RN BANERJEE A MCNAMEE CG BRZOZOWSKI DB SZARKA LJ
Citation
Rn. Patel et al., PREPARATION OF CHIRAL SYNTHON FOR HIV PROTEASE INHIBITOR - STEREOSELECTIVE MICROBIAL REDUCTION OF N-PROTECTED ALPHA-AMINOCHLOROKETONE, Tetrahedron : asymmetry, 8(15), 1997, pp. 2547-2552
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
8
Issue
15
Year of publication
1997
Pages
2547 - 2552
Database
ISI
SICI code
0957-4166(1997)8:15<2547:POCSFH>2.0.ZU;2-E
Abstract
The chiral intermediate (1S,2R) [3-chloro-2-hydroxy-1-(phenylmethyl)pr opyl] carbamic acid, 1,1-dimethylethyl ester 2a was prepared for the t otal synthesis of an HIV protease inhibitor, BMS-186318. The stereosel ective reduction of (1S) [3-chloro-2-oxo-1-(phenylmethyl)propyl] carba mic acid, 1,1-dimethyl-ethyl ester 1 was carried out using microbial c ultures among which Streptomyces nodosus SC 13149 efficiently reduced 1 to 2a. A reaction yield of 80% was obtained. The optical purity of 9 9.8% and the diastereomeric purity of 99% were obtained for chiral alc ohol 2a. (C) 1997 Elsevier Science Ltd.