AN EFFICIENT ASYMMETRIC-SYNTHESIS OF THE MERCAPTOPYRROLIDINE SIDE-CHAIN OF AN IMPORTANT BETA-METHYL CARBAPENEM ANTIBIOTIC

Authors
ARMSTRONG JD KELLER JL LYNCH J LIU T HARTNER FW OHTAKE N OKADA S IMAI Y OKAMOTO O USHIJIMA R NAKAGAWA S VOLANTE RP
Citation
Jd. Armstrong et al., AN EFFICIENT ASYMMETRIC-SYNTHESIS OF THE MERCAPTOPYRROLIDINE SIDE-CHAIN OF AN IMPORTANT BETA-METHYL CARBAPENEM ANTIBIOTIC, Tetrahedron letters, 38(18), 1997, pp. 3203-3206
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
18
Year of publication
1997
Pages
3203 - 3206
Database
ISI
SICI code
0040-4039(1997)38:18<3203:AEAOTM>2.0.ZU;2-J
Abstract
An efficient asymmetric synthesis of the mercaptopyrrolidine side chai n 2 Is described The beta-ketoester 4 is hydrogenated diastereoselecti vely to give the (R)-beta-hydroxyester 5. The remaining functional gro ups are installed via a thiol Mitsunobu reaction and a reduction of a secondary amide to produce 2 in 34% overall yield from BOC-L-trans-4-h ydroxyproline methylester 3 (Scheme 1). (C) 1997 Elsevier Science Ltd.