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Paper | Regular issue | Vol 31, No. 1, 1990, pp.139-147
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5208
Unexpected Reaction between DCC and Cephalosporanic Acid Sulphones

Marco Alpegiani, Pierluigi Gissolino, Emanuele Arlandini, Daniela Borghi, and Ettore Perrone

*Farmitalia Carlo Erba, R&D, Infectious Diseases Dep., Via dei Gracchi 35, 20146 Milano, Italy

Abstract

Cephalosporanic acid sulphones react with DCC to give a novel 4-spiroazetidinyl-Δ2-cephem structure with high stereoselectivity. The reaction, though general for cephem-4-carboxylic acids, is deeply affected by oxidation at sulphur; an external base was required for the 1-sulphide 3, and stereoselectivity was lost with the 1α-sulphoxide 9.