Efficient Synthetic Access to the Hetisine C20-Diterpenoid Alkaloids. A Concise Synthesis of Nominine via Oxidoisoquinolinium-1,3-Dipolar and Dienamine-Diels−Alder Cycloadditions

Kevin M. Peese and David Y. Gin*†
Department of Chemistry, University of Illinois, Urbana, Illinois 61801
J. Am. Chem. Soc., 2006, 128 (27), pp 8734–8735
DOI: 10.1021/ja0625430
Publication Date (Web): June 17, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

,
†

 Address correspondence to:  Department of Molecular Pharmacology and Chemistry, The Sloan-Kettering Institute, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY 10021.

, gind@mskcc.org

Abstract

Abstract Image

A concise synthetic approach to the hetisine C20-diterpenoid alkaloids is reported. The total synthesis of (±)-nominine was accomplished in a 15-step sequence employing a dual cycloaddition strategy. Key features of the synthesis include a reversible intramolecular 4-oxidoisoquinolinium betaine dipolar cycloaddition in conjunction with a pyrrolidine-induced dienamine isomerization/Diels−Alder cascade.

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History

  • Published In Issue July 12, 2006
  • Received April 12, 2006

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