We gratefully acknowledge the University of Illinois at Chicago for their support. We thank Dr. Furong Sun (UIUC) for mass spectrometry measurements.
Concise Synthesis of the Tricyclic Core of Platencin†
Article first published online: 11 JUN 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 33, pages 6201–6203, August 4, 2008
How to Cite
Yun, S., Zheng, J.-C. and Lee, D. (2008), Concise Synthesis of the Tricyclic Core of Platencin. Angew. Chem. Int. Ed., 47: 6201–6203. doi: 10.1002/anie.200801587
- Issue published online: 29 JUL 2008
- Article first published online: 11 JUN 2008
- Manuscript Received: 4 APR 2008
- natural products;
- radical cyclization;
- ring-closing metathesis;
- total synthesis
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).