Download PDF
Synlett 1999; 1999(S1): 909-912
DOI: 10.1055/s-1999-3111
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Trials for the Synthesis of (R)-4-Mercapto-pyrrolidin-2-one ((R)-MPD)

Satoshi Kobayashi* , Katsuhiro Kobayashi, Koichi Hirai
  • *Process Development Laboratories, Sankyo Co., Ltd. No. 173, Nakahara-Kamijuku, Hiratsuka-shi, Kanagawa 254-0071, Japan; Fax +81(4 63)31 65 25; E-mail: khirai@hira.sankyo.co.jp
Further Information

Publication History

Publication Date:
31 December 1999 (online)

  PDF Download  Permissions and Reprints All articles of this category

Several trials were made for the syntheses of (S)-4-hydroxy-pyrrolidin-2-one ((S)-HPD) and (R)-4-mercapto-pyrrolidin-2-one ((R)-MPD), a substituent at the 2-position of the orally active carbapenem antibiotic CS-834. The latter was synthesized from prochiral dimethyl or diethyl 3-p-methoxybenzylthioglutarate using pig liver esterase technology to give monoester with an optical purity of 51-71% e.e. as a key intermediate.

γ-lactam formation - 4-mercapto-pyrrolidone - pig liver esterase - intramolecular Schmidt reaction - Curtius rearrangement - 4-hydroxy-pyrrolidone - CS-834