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Paper | Regular issue | Vol 45, No. 2, 1997, pp.265-270
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7626
Synthesis of Dioxolanylclavam from Tartaric Acid

Oliver Neuß, Bartlomiej Furman, Zbigniew Kaluza, and Marek Chmielewski*

*Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O. Box 58, 01-244 Warsaw, Poland

Abstract

[2+2] Cycloaddition of chlorosulfonyl isocyanate ot the 3-O-vinyl ether (8) derived from tartaric acid provides 4-alkoxy-azetidin-2-one (9) with 91.0% d.e.. Intramolecular N-alkylation afforded clavam (11) which corresponds to clavulanic acid missing the C-3 carboxylic function.