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
Citation
T. Hashihayata et al., Diastereoselective synthesis of (2R,4R)-2-aryl-4-hydroxypyrrolidine: Preparation of the side chain of novel carbapenem, CHEM PHARM, 49(11), 2001, pp. 1500-1502
Citations number
6
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
49
Issue
11
Year of publication
2001
Pages
1500 - 1502
Database
ISI
SICI code
0009-2363(200111)49:11<1500:DSO(P>2.0.ZU;2-C
Abstract
Improved synthesis of the tratis-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 cycliz ation 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.