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Diastereoselective synthesis of (2R,4R)-2-aryl-4-hydroxypyrrolidine: preparation of the side chain of novel carbapenem.

Authors
  • Hashihayata, T
  • Sakoh, H
  • Goto, Y
  • Hirose, M
  • Sakuraba, S
  • Imamura, H
  • Sugimoto, Y
  • Yamada, K
  • Morishima, H
Type
Published Article
Journal
Chemical & pharmaceutical bulletin
Publication Date
Nov 01, 2001
Volume
49
Issue
11
Pages
1500–1502
Identifiers
PMID: 11724250
Source
Medline
License
Unknown

Abstract

Improved synthesis of the trans-3,5-disubstituted pyrrolidin-3-ylthio side-chain of the novel carbapenem 1 was achieved via stereoselective reduction of the 1-aryl-1-butanone derivative 5 and successive intramolecular cyclization of the resulting chiral alcohol 6. The 1-aryl-1-butanone derivative 5 was obtained by a coupling reaction of protected 4-hydroxy-2-pyrrolidone with aryl-Grignard reagent.

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