Bisavenanthramide B is a highly substituted γ-lactam derived from oat leaves exposed to various pathogens. Herein we present the development of a new base promoted anhydride Mannich reaction with <i>N</i>-sulfonylated imines that forms the core structure of Bisavenanthramide B in a single step with high diastereoselectivity and complete control of the exocyclic alkene geometry. Further elaboration allows for a facile one-pot double Buchwald coupling to install the final two aryl rings onto the densely substituted γ-lactam core. This route allows for a nearly isohypsic synthesis of the natural product in nine steps longest linear sequence (11 steps total).

New anhydride Mannich reaction: The total synthesis of bisavenanthramide B

251st National Meeting (2016)

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