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Synfacts 2009(4): 0352-0352  
DOI: 10.1055/s-0028-1088092
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Sesquisabinene and Epoxysesquithujene

Contributor(s): Philip Kocienski, Arndt W. Schmidt
A. Fürstner*, A. Schlecker
Max-Planck-Institut für Kohlenforschung, Mülheim an der Ruhr, Germany
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Publikationsdatum:
23. März 2009 (online)

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Significance

Ohloff and co-workers (Helv. Chim. Acta 1976, 1328) and Rautenstrauch (J. Org. Chem. 1984, 84, 950) were the first to report Lewis acid induced enyne cycloisomerizations with migratory participation of a propargylic ester. Using a gold(III)-π-Lewis acid as promoter, a new entry to the sesquisabinenes and sesquithujenes is described. These terpenes are isolated from various plants such as pepper, ginger or Himala­yan herbs used in folk medicine. More importantly, some are constituents of pheromones of pestilent insects.