ChemInform Abstract: Synthesis of Dioxolanylclavam from Tartaric Acid.

✍ Scribed by O. NEUSS; B. FURMAN; Z. KALUZA; M. CHMIELEWSKI

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 30 KB
• Volume: 28
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199734280

✦ Synopsis

Synthesis of Dioxolanylclavam from Tartaric Acid. -(2 + 2) Cycloaddition of the 3-O-vinyl ether (I) derived from tartaric acid to chlorosulfonyl isocyanate (II) gives the 4-alkoxyazetidinone ( III) with good diastereoselectivity. Cyclization provides the clavam ( IV) missing the C-3 carboxylic function of clavulanic acid. It shows no antibacterial effects but anti β-lactamase activity. -(NEUSS, O.; FURMAN, B.; KALUZA, Z.;