Synthesis of Putative Uniflorine A

Andrew S. Davis,† Stephen G. Pyne,*† Brian W. Skelton,‡ and Allan H. White‡
Department of Chemistry, University of Wollongong, Wollongong, New South Wales, 2522, Australia, and Department of Chemistry, University of Western Australia, Crawley, Western Australia, 6009, Australia
J. Org. Chem., 2004, 69 (9), pp 3139–3143
DOI: 10.1021/jo049806y
Publication Date (Web): April 2, 2004
Copyright © 2004 American Chemical Society
†

 University of Wollongong.

,
*

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

,
‡

 University of Western Australia.

, spyne@uow.edu.au

Abstract

Abstract Image

A diastereoselective synthesis of the putative structure of the natural product uniflorine A has been achieved by using the Petasis borono−Mannich reaction and ring-closing metathesis as key steps. The NMR data of the synthetic material did not match that reported for the natural product. The structure of the final synthetic product was unequivocally determined by single-crystal X-ray study of its pentaacetate derivative. Thus it was concluded that the proposed structure of uniflorine A is incorrect.

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History

  • Published In Issue April 30, 2004
  • Received February 2, 2004

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