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Paper | Regular issue | Vol 26, No. 4, 1987, pp.1001-1013
Published online, 1st January, 1970
DOI: 10.3987/R-1987-04-1001
Chemistry of Penicillin Diazoketones. Part III. Transformation of Tricyclic Beta-lactams

Ching-Pong Mak, Gerhard Schulz, and Hans Fliri

*Sandoz Forschungsinstitut, 1235 Wien, Brunnerstraße 59, Austria

Abstract

The transformation of tricyclic beta-lactams 1a-c, which are obtained from the corresponding penicillin diazoketones, into carbapenams 7-11 are described. Whereas reduction of 1c with tetra-n-butylammonium borohydride gave cleanly the hydmxy-lactam 3c, the isomeric ketone 1b yielded 3c, together with two tricyclic lactones 5a/b Azido-lactones 5c/d were obtained similarly when we reacted 1b with aluminium chloride/sodium azide. The structural assignment of these novel compounds was based mainly on spectroscopic analysis and comparison with the corresponding tricyclic lactam 3c.