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Synfacts 2007(3): 0242-0242  
DOI: 10.1055/s-2007-968196
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Guanacastepene N

Contributor(s): Philip Kocienski, Thomas Snaddon
S. Iimura, L. E. Overman*, R. Paulini, A. Zakarian
University of California, Irvine, USA
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Publication History

Publication Date:
20 February 2007 (online)

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Significance

The guanacastepenes are a family of complex diterpenes that have inspired widespread synthetic interest due to their unusual fused 5-7-6 tricyclotetradecane ring system and their pronounced antibacterial action. Noteworthy in this synthesis of guanacastepene N is (a) the conjugate addition of a cyanocuprate to a sterically congested enone, and (b) an unusual Heck reaction that proceeds via a 7-endo-trig cyclization.

Reviews: For a discussion of the Heck reaction in target-directed synthesis, see: A. B. Dounay, L. E. Overman Chem. Rev. 2003, 103, 2945-2963.