Bioinspired synthesis of a lactam analogue of abyssomicin C

Abstract

The bioinspired approach to abyssomicin C developed by Sorensen has been utilized to prepare a novel analog containing an α, β-unsaturated lactam. This synthesis was designed to utilize the intramolecular Diels-Alder reaction in late-stage synthesis to provide analogs that contain deep-seated modifications to explore their antimicrobial properties. Overall, installing this non-natural lactam moiety was successful and allowed for antimicrobial assessment of the analog, but the low yields highlight the frequent challenges of leveraging a bioinspired approach for a new-to-nature molecular target.