Direct Conversion of N-Alkoxy β-Lactams to Carbapenams: Application to the Synthesis of the Bicyclic PS-5 Keto Ester

Article abstract of DOI:10.1021/jo00008a022

The synthesis and direct conversion of N-alkoxy β-lactams to the carbapenam ring system is described.This novel cyclization apparently proceeds by initial carbene-mediated ylide formation with concomitant rearrangement.The title reaction is applied to the construction of the methyl ester of the bicyclic β-lactam precursor of PS-5.