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Synfacts 2010(5): 0511-0511  
DOI: 10.1055/s-0029-1219714
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Mersicarpine

Contributor(s): Steven V. Ley, Kimberley A. Roper
R. Nakajima, T. Ogino, S. Yokoshima, T. Fukuyama*
The University of Tokyo, Japan
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Publication History

Publication Date:
22 April 2010 (online)

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Significance

(-)-Mersicarpine has an atypical tetracyclic structure where three heterocycles are fused around a tertiary hydroxyl group. This is the first enantioselective synthesis and utilizes an ­Eschenmoser-Tanabe-type fragmentation, a gold(III)-catalyzed cyclization and finally a three-step, one-pot process to close the seven-membered ring and install the hemiaminal moiety.