We thank Dr. D.-H. Huang and Dr. L. Pasternack for NMR spectroscopic assistance, Dr. G. Siuzdak for mass spectrometric and Dr. Arnold Rheingold (UCSD) for X-ray crystallographic assistance. Financial support for this work was provided by Bristol-Myers Squibb (predoctoral fellowship to T. J. M.), Merck, and Roche.
A Concise Approach to Vinigrol†
Article first published online: 12 MAR 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 16, pages 3054–3056, April 7, 2008
How to Cite
Maimone, Thomas J., Voica, A.-F. and Baran, Phil S. (2008), A Concise Approach to Vinigrol. Angew. Chem. Int. Ed., 47: 3054–3056. doi: 10.1002/anie.200800167
- Issue published online: 1 APR 2008
- Article first published online: 12 MAR 2008
- Manuscript Received: 13 JAN 2008
- cascade reactions;
- natural products;
- total synthesis;
Short and sweet: A simple and practical route to the unusual tricyclic ring system found in the biologically active diterpene vinigrol is described. A remarkable proximity-induced intramolecular cycloaddition and mild Grob fragmentation allow rapid construction of the core ring system in less than 10 steps and with a minimal reliance on protecting groups.