Concise Synthesis of the Tricyclic Core of Platencin


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


original image

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).