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Concise Synthesis of the Tricyclic Core of Platencin

Authors


  • We gratefully acknowledge the University of Illinois at Chicago for their support. We thank Dr. Furong Sun (UIUC) for mass spectrometry measurements.

Abstract

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A radical change: Implementation of a radical-mediated rearrangement of the bicyclo[3.2.1]octyl moiety to the bicyclo[2.2.2]octane structure has enabled a concise synthesis of the tricyclic core of platencin, a newly discovered antibiotic. An intramolecular aldol and a ring-closing metathesis reaction were subsequently used to complete the synthesis of the tricycle (see scheme).

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