We thank Dr. J. Lee (Boston University) for assistance with NMR experiments and the National Institutes of Health (GM-62842) for research support.
Synthesis of the Tetracyclic Core of the Tetrapetalones through Transannular Oxidative [4+3] Cyclization†
Article first published online: 14 APR 2005
Copyright © 2005 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 44, Issue 20, pages 3067–3071, May 13, 2005
How to Cite
Wang, X. and Porco, J. A. (2005), Synthesis of the Tetracyclic Core of the Tetrapetalones through Transannular Oxidative [4+3] Cyclization. Angew. Chem. Int. Ed., 44: 3067–3071. doi: 10.1002/anie.200500247
- Issue published online: 9 MAY 2005
- Article first published online: 14 APR 2005
- Manuscript Received: 21 JAN 2005
Vol. 45, Issue 40, 6607, Article first published online: 10 OCT 2006
A convergent strategy involving a base-mediated silyl transfer/acylation for fragment coupling and a tandem process consisting of nitro reduction and acyl transfer can be employed to construct strained, bicyclic macrolactams (see scheme). The tetracyclic core of the tetrapetalones, which are effective lipoxygenase inhibitors, can be prepared by using an IIII-promoted cyclization.