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A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one as a taxol side chain precursor

Authors: Song, CE; Lee, SW; Roh, EJ; Lee, SG; Lee, WK

Issue Date: 1998-03-27

Publisher: PERGAMON-ELSEVIER SCIENCE LTD

Citation: TETRAHEDRON-ASYMMETRY, v.9, no.6, pp.983 - 992

Abstract: A new synthetic route to (3R,4S)-3-hydroxy-4-phenylazetidin-2-one an important precursor for the paclitaxel side chain, has been developed using intramolecular cyclization of N-(p-methoxyphenyl) (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionamide which can be easily obtained by catalytic asymmetric dihydroxylation of N-(p-methoxyphenyl)-trans-cinnamide, followed by bromoacetylation. (C) 1998 Elsevier Science Ltd. All rights reserved.

Keywords: LACTAM SYNTHON METHOD; ALPHA-HYDROXY ACIDS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC DIHYDROXYLATION; AMINO-ACIDS; BETA-AMINO; HETEROGENEOUS MEDIA; HIGHLY EFFICIENT; TAXOTERE; N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE; LACTAM SYNTHON METHOD; ALPHA-HYDROXY ACIDS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC DIHYDROXYLATION; AMINO-ACIDS; BETA-AMINO; HETEROGENEOUS MEDIA; HIGHLY EFFICIENT; TAXOTERE; N-BENZOYL-(2R,3S)-3-PHENYLISOSERINE; taxol

ISSN: 0957-4166

URI: https://pubs.kist.re.kr/handle/201004/143173

DOI: 10.1016/S0957-4166(98)00049-4

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