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Paper | Special issue | Vol 30, No. 2, 1990, pp.863-869
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S68
The Synthesis of Carbapenem and Carbacephem Derivatives by a Combination of 4CC with the Chemistry of Oxazoles and N-Boc-carbonamides

Gebhard Neyer, Josef Achatz, Bernhard Danzer, and Ivar Ugi*

*Organisch-Chemisches Institut der Techmisches, Universität München, Münvhen, D-8046 Garching, Germany

Abstract

A synthetic approach to carbapenem and carbacephem derivatives is described. It is based on the formation of the N-carboxymethyl-β-lactam system by a four component condensation, the cleavage of a carbonamide via the N-Boc-carbonamides and esters, and the masking of a carboxyl group as its 4,5-diphenyloxazolyl derivative that is convertible to an N,N-dibenzoylamide by photooxidation.