RING EXPANSION OF NORPENICILLIN TO 3-NORCEPHALOSPORIN

Authors
VANDERKLEIN PAM CASTELIJNS J HIRS HGJ VERWEIJ J DEVROOM E
Citation
Pam. Vanderklein et al., RING EXPANSION OF NORPENICILLIN TO 3-NORCEPHALOSPORIN, Recueil des travaux chimiques des Pays-Bas, 115(3), 1996, pp. 185
Citations number
18
Categorie Soggetti
Chemistry
Journal title
Recueil des travaux chimiques des Pays-Bas → ACNP
ISSN journal
01650513
Volume
115
Issue
3
Year of publication
1996
Database
ISI
SICI code
0165-0513(1996)115:3<185:REONT3>2.0.ZU;2-R
Abstract
The Morin ring expansion of penicillin 1-oxides to cephalosporins has been extended to norpenicillin 1-oxides. To this end, both the norpeni cillin sulfoxide moiety and the methyl group should be beta-oriented. Norpenicillin 1-oxides are prepared from properly protected exomethyle ne penam derivatives using hydrogen on palladium/carbon and oxidation with 3-chloroperoxybenzoic acid or peroxyacetic acid.