Concise Total Synthesis of (+)-WIN 64821 and (−)-Ditryptophenaline


  • 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.


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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.