Diastereoselective Synthesis of the Carbacephem Framework

Article abstract of DOI:10.1021/jo00055a013

A short, versatile, and diastereoselective method of preparing carbacephems has been developed.The procedure involves as a key step the aldol condensation of a protected glycine compound with a suitably designed aldehyde.In this step, most of the carbon skeleton of the carbacephem is assembled, and the two stereocenters of the final β-lactam are set.This step also provides well-placed and synthetically useful functionality for further elaboration into the desired target.