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Synfacts 2007(5): 0462-0462  
DOI: 10.1055/s-2007-968398
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (±)-Vigulariol

Contributor(s): Philip Kocienski, Zofia Komsta
J. S. Clark*, S. T. Hayes, C. Wilson, L. Gobbi
University of Glasgow and University of Nottingham, UK; F. Hoffmann-La Roche Ltd., Basel, Switzerland
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Publication History

Publication Date:
24 April 2007 (online)

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Significance

The cladiellin diterpene vigulariol displays in vitro cytoxicity against human lung ­adenocarcinoma cells. This synthesis exploits the [2,3]-sigmatropic rearrangement of an oxonium ylide to construct the oxabicyclo[6.2.1]undecane core.