Stereoselective synthesis of a broad spectrum 1 beta-methylcarbapenem, J-114,870

Authors
Imamura, H Shimizu, A Sato, H Sugimoto, Y Sakuraba, S Nakajima, S Abe, S Miura, K Nishimura, I Yamada, K Morishima, H
Citation
H. Imamura et al., Stereoselective synthesis of a broad spectrum 1 beta-methylcarbapenem, J-114,870, TETRAHEDRON, 56(39), 2000, pp. 7705-7713
Citations number
22
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
39
Year of publication
2000
Pages
7705 - 7713
Database
ISI
SICI code
0040-4020(20000922)56:39<7705:SSOABS>2.0.ZU;2-T
Abstract
An ultra-broad spectrum carbapenem, J-114,870 (1), was synthesized from the corresponding C-2 side chain and 1 beta-methyl carbapenem enolphosphate. S ynthesis of the C-2 side chain was accomplished by installation of the benz ene part to (4R)-hydroxy-2-pyrrolidone 3, affording 2-phenylpyrrolidine 8a, and asymmetric Michael addition of chiral amine to alpha,beta-unsaturated ester derived from 8a. (C) 2000 Elsevier Science Ltd. All rights reserved.