SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .5. EFFICIENT SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM SKELETON

Authors
SUNAGAWA M SASAKI A MATSUMURA H GODA K TAMOTO K
Citation
M. Sunagawa et al., SYNTHETIC STUDIES OF CARBAPENEM AND PENEM ANTIBIOTICS .5. EFFICIENT SYNTHESIS OF THE 1-BETA-METHYLCARBAPENEM SKELETON, Chemical and Pharmaceutical Bulletin, 42(7), 1994, pp. 1381-1387
Citations number
20
Categorie Soggetti
Pharmacology & Pharmacy",Chemistry
Journal title
Chemical and Pharmaceutical Bulletin → ACNP
ISSN journal
00092363
Volume
42
Issue
7
Year of publication
1994
Pages
1381 - 1387
Database
ISI
SICI code
0009-2363(1994)42:7<1381:SSOCAP>2.0.ZU;2-#
Abstract
An efficient synthesis of 1 beta-methylcarbapenem from the 1-(2-oxoaze tidinyl)acetate 8 was developed by application of the Dieckmann reacti on. Dieckmann-type cyclization of 8 and conversion to the enolphosphat e 10 were achieved without epimerization to the 1 alpha-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phos phorylation resulted in a practical one-pot preparation of the 1 beta- methylcarbapenem derivative 23 from 8.