SYNTHESIS OF DIOXOLANYLCLAVAM FROM TARTARIC ACID

Authors
NEUB O FURMAN B KALUZA Z CHMIELEWSKI M
Citation
O. Neub et al., SYNTHESIS OF DIOXOLANYLCLAVAM FROM TARTARIC ACID, Heterocycles, 45(2), 1997, pp. 265-270
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
45
Issue
2
Year of publication
1997
Pages
265 - 270
Database
ISI
SICI code
0385-5414(1997)45:2<265:SODFTA>2.0.ZU;2-L
Abstract
[2+2] Cycloaddition of chlorosulfonyl isocyanate to the 3-O-vinyl ethe r (8) derived from tartaric acid provides 4-alkoxy-azetidin-2-one (9) with 91.0% d.e.. Intramolecular N-alkylation afforded clavam (11) whic h corresponds to clavulanic acid missing the C-3 carboxylic function.