Synthesis of (−)-Haliclonadiamine

Douglass F. Taber* and Yanong Wang
Contribution from the Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19176
J. Am. Chem. Soc., 1997, 119 (1), pp 22–26
DOI: 10.1021/ja962162u
Publication Date (Web): January 8, 1997
Copyright © 1997 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.

Abstract

Diastereoselective and enantioselective hydrogenation of the racemic β-keto ester 5 to give the enantiomerically pure (96% ee) ester 8 is reported. The conversion of the derived vinylstannane 11 to the antibiotic marine alkaloid (−)-haliclonadiamine (1) is described.

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History

  • Published In Issue January 08, 1997
  • Received June 26, 1996

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