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Synfacts 2009(7): 0712-0712  
DOI: 10.1055/s-0029-1217239
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Cassiol

Contributor(s): Philip Kocienski, Indu Dager
K. V. Petrova, J. T. Mohr, B. M. Stoltz*
California Institute of Technology, Pasadena, USA
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

An enantioselective total synthesis of the antiulcerogenic natural product (+)-cassiol starts with a vinylogous thioester A and employs a catalytic enantioselective decarboxylative allylation to yield the quaternary center in ketone D. The reaction has also been used in the total synthesis of (+)-carissone (Org. Lett. 2009, 11, 289).