PRACTICAL SYNTHESIS OF PENEMS AND CARBAPENEMS KEY INTERMEDIATE

Authors
SEKI M MIYAKE T YAMANAKA T OHMIZU H
Citation
M. Seki et al., PRACTICAL SYNTHESIS OF PENEMS AND CARBAPENEMS KEY INTERMEDIATE, Synlett, (5), 1996, pp. 455
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synlett → ACNP
ISSN journal
09365214
Issue
5
Year of publication
1996
Database
ISI
SICI code
0936-5214(1996):5<455:PSOPAC>2.0.ZU;2-P
Abstract
Titanium enolate-mediated aldol reaction of chiral N-phthaloyl-beta-al anyl-1,3-benzoxazinone 5 with acetaldehyde furnished the (2S,3R)-syn-a ldol 6 in high yield with high stereoselectivity. Silylation of the hy droxy group of 6 followed by removal of the protective groups and cycl ization gave the optically pure beta-lactam 9 which was transformed in to the acetoxyazetidinone 3, a key intermediate of penems and carbapen ems.