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| - Design and Synthesis of a Novel Class of Constrained TricyclicPyrrolizidinone Carboxylic Acids as Carbapenem Mimics
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| - A series of tricyclic pyrrolizidinone carboxylic acids harboring an angular methano group weresynthesized as mimics of carbapenems and carbapenams. A key reaction involved a novelintramolecular cyclopropanation mediated by a trimethylstannylmethyl group and an adjacentiminium ion. Enolate chemistry on a tricyclic lactam ring unit allowed the introduction of varioussubstituents. Further elaboration afforded tricyclic pyrrolidinone carboxylic acids, which were foundto be inactive as inhibitors against a panel of bacterial strains. However, the antibacterial activityof ceftazidine was enhanced in the presence of the tricyclic analogues.
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