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Synfacts 2009(9): 0952-0952  
DOI: 10.1055/s-0029-1217620
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Spicigerolide

Contributor(s): Philip Kocienski, Zofia Komsta
Y. Georges, X. Ariza*, J. Garcia*
Universitat de Barcelona, Spain
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Publication History

Publication Date:
21 August 2009 (online)

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Significance

Spicigerolide was isolated from Hyptis spicigera, a Mexican plant used in traditional medicine to treat gastrointestinal problems, skin infections, wounds, and insect bites. An interesting step of the synthesis is a regiocontrolled palladium-catalyzed [3,3]-sigmatropic rearrangement D → E. The Carreira alkynylation was deployed twice in the synthesis.