Lovji D. Cama

Synthetic carbapenem antibiotics III. 1-Methyl thienamycin

Total syntheses of 1α- and 1β-methyl thienamycin are reported. 1β-Methyl thienamycin retains the antibacterial activity of thienamycin and is highly resistant to hydrolysis by DHP-I enzyme.

Synthesis and activity of 2-(sulfonamido)methyl-carbapenems: Discovery of a novel, anti-MRSA 1,8-naphthosultam pharmacophore

A series of 1beta-methyl carbapenems substituted at the 2-position with lipophilic, acyclic and cyclic (sulfonamido)methyl groups was prepared and evaluated for activity against resistant gram-positive bacteria. From these studies, the 1,8-naphthosultamyl group emerged as a novel, PBP2a-binding, anti-MRSA pharmacophore worthy of further exploration.

Total synthesis of thienamycin analogs. II Synthesis of 2-alkyl and 2-aryl thienamycin nuclei

Abstract A new general synthesis leading to 2-alkyl and 2-aryl-1-carba-2-penem-3-carboxylic acids involves the preparation of a key thiolester intermediate 3. This is reacted with Me2CuLi or (C6H5)2MgCuX to give the corresponding methyl or phenyl ketone which undergoes a Wittig reaction to give the desired penems, which can be deblocked photolytically or by hydrogenolysis to give acids with good antibacterial activity.