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Synfacts 2008(2): 0124-0124  
DOI: 10.1055/s-2007-992500
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (+)-Fawcettimine

Contributor(s): Philip Kocienski
X. Linghu, J. J. Kennedy-Smith, F. D. Toste*
University of California, Berkeley, USA
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

A 13-step synthesis of the Lycopodium alkaloid (+)-fawcettimine from crotonaldehyde is described that features a gold(I)-catalyzed 5-endo-dig cyclization of an enolsilane D onto a 1-iodoalkyne to generate an iodocyclopentene ring E. The iodocyclopentene then serves as a substrate in a Suzuki-Miyaura cross-coupling (E→F).