Gregg Brian Feigelson

A new strategy for the synthesis of carbapenems. A formal total synthesis of (+)-thienamycin.

Abstract A new approach to formation of the carbapenem ring system is presented. The key step involves the Lewis acid mediated cyclocondensation of a β-lactam nitrogen and the α-keto ester of a suitably disposed side-chain. The preparation of a known and pivotal intermediadate in the synthesis of thienamycin serves to demonstrate this strategy.

An intramolecular addition-elimination strategy for the synthesis of carbapenems

Abstract The synthesis of 2-[(4-fluorophenylsulfonyl)methyl] carbapenem carboxylate 20 is described. The key step is a base mediated addition-elimination ring closure of a iodovinyl sulfone 12.

Process Improved Preparation of a Versatile α-Ketoester Acyl Anion Synthon

Abstract An improved scalable procedure for preparation of an α-ketoester acyl anion synthon is described.