We thank Cornell University and the NIH (CBI Training Grant (N.A.M. and M.B.) for financial support. We also thank Dr. Ivan Keresztes (Cornell) for assistance with NMR spectroscopy.
An Efficient Substrate-Controlled Approach Towards Hypoestoxide, a Member of a Family of Diterpenoid Natural Products with an Inside-Out [9.3.1]Bicyclic Core†
Article first published online: 31 OCT 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 49, pages 9450–9453, November 24, 2008
How to Cite
McGrath, Nicholas A., Lee, Christopher A., Araki, H., Brichacek, M. and Njardarson, Jon T. (2008), An Efficient Substrate-Controlled Approach Towards Hypoestoxide, a Member of a Family of Diterpenoid Natural Products with an Inside-Out [9.3.1]Bicyclic Core. Angew. Chem. Int. Ed., 47: 9450–9453. doi: 10.1002/anie.200804237
- Issue published online: 20 NOV 2008
- Article first published online: 31 OCT 2008
- Manuscript Revised: 19 SEP 2009
- Manuscript Received: 27 AUG 2008
- natural products;
- total synthesis
The bicycle works: A versatile route to the verticillane family of natural products has been devised, utilizing a strategically rigidified relay ring-closing metathesis reaction. The shape of the bicyclic product was used to stereoselectively control the bisepoxidation reaction towards hypoestoxide, a member of this natural product family.