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Synfacts 2009(6): 0587-0587  
DOI: 10.1055/s-0029-1216678
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Serotobenine

Contributor(s): Philip Kocienski, Zofia Komsta
Y. Koizumi, H. Kobayashi, T. Wakimoto, T. Furuta, T. Fukuyama*, T. Kan*
University of Shizuoka and the University of Tokyo, Japan
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Publication History

Publication Date:
25 May 2009 (online)

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Significance

Serotobenine is isolated in its racemic form from the seeds of the safflower Carthamus tincorius L. The noteworthy step of the synthesis is the high-yielding and stereoselective rhodium-catalyzed C-H insertion reaction (G → H). The asymmetric induction is more dependent on the chiral auxiliary rather than on the catalyst.