Further Studies of the Daphniphyllum Alkaloid Polycyclization Cascade

Grier A. Wallace and Clayton H. Heathcock*
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720
J. Org. Chem., 2001, 66 (2), pp 450–454
DOI: 10.1021/jo001145r
Publication Date (Web): December 23, 2000
Copyright © 2001 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.

, heathcock@cchem.berkeley.edu

Abstract

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The scope of the 2-azadiene intramolecular Diels−Alder cyclization, previously employed for synthesis of the Daphniphyllum alkaloids, has been further investigated. Through a series of 1,5-diol cyclization precursors the substitution pattern of both the dienophile and the 2-azadiene were examined. From these studies it was shown that the cascade reaction is tolerant toward a variety of alkyl-substituted dienophiles. However, it was also demonstrated that this reaction is very sensitive to the substitution pattern of the 2-azadiene. Alterations made to the structure of the 2-azadiene cause either competing side reactions or complete failure of the reaction cascade.

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History

  • Published In Issue January 26, 2001
  • Received July 28, 2000

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