M.M. is a Beckman Young Investigator. J.A.A. acknowledges a postdoctoral fellowship from Fonds Québécois de la Recherche sur la Nature et les Technologies. We are grateful to Prof. L. E. Overman for a copy of the 1H NMR spectrum of (−)-1. We acknowledge generous support from Amgen, GlaxoSmithKline, Boehringer Ingelheim Pharmaceutical Inc., and Merck Research Laboratories.
Concise Total Synthesis of (+)-WIN 64821 and (−)-Ditryptophenaline†
Article first published online: 11 JAN 2008
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 47, Issue 8, pages 1485–1487, February 8, 2008
How to Cite
Movassaghi, M., Schmidt, Michael A. and Ashenhurst, James A. (2008), Concise Total Synthesis of (+)-WIN 64821 and (−)-Ditryptophenaline. Angew. Chem. Int. Ed., 47: 1485–1487. doi: 10.1002/anie.200704960
- Issue published online: 4 FEB 2008
- Article first published online: 11 JAN 2008
- Manuscript Received: 26 OCT 2007
- Fonds Québécois de la Recherche sur la Nature et les Technologies
- Boehringer Ingelheim Pharmaceutical Inc.
- Merck Research Laboratories
- total synthesis
On a fast track: The secondary metabolites (+)-WIN 64821 and (−)-ditryptophenaline have been synthesized in six and seven steps, respectively, from amino acid derivatives in a concise and enantioselective manner. The gram-scale synthesis of key intermediates and the simultaneous introduction of vicinal quaternary stereocenters are described. The synthesis and structural confirmation of (−)-1′-(2-phenylethylene)ditryptophenaline is also reported.