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Synfacts 2008(12): 1254-1254  
DOI: 10.1055/s-0028-1087287
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Incarvillateine

Contributor(s): Philip Kocienski, Zofia Komsta
A. S. Tsai, R. G. Bergman*, J. A. Ellman*
University of California, Berkeley, USA
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Publication History

Publication Date:
20 November 2008 (online)

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Significance

Incarvillateine is an alkaloid extracted from the Chinese plant Incarvillea sinensis, used in folk medicine for treating rheumatism and as a pain killer. The compound showed some potent analgesic properties and probably works via an adenosine receptor mechanism. This concise synthesis features a Rh-catalyzed intramolecular alkylation, installing two stereogenic centers (D → H).