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Total synthesis of (-)-mersicarpine
Rie Nakajima1, Tsuyoshi Ogino, Satoshi Yokoshima
1Graduate School of Pharmaceutical Sciences, University of Tokyo,7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Abstract:
The total synthesis of (-)-mersicarpine was achieved in 10 steps from a known ketoester. Our synthesis features an Eschenmoser-Tanabe-type fragmentation to synthesize an alkyne unit containing a quaternary carbon center, a facile construction of the indole skeleton via a combination of a Sonogashira coupling and a gold(III) catalyzed cyclization, as well as a one-pot process to arrange the cyclic imine and the hemiaminal moieties. Our synthesis unambiguously confirmed the reported structure of (-)-mersicarpine including the absolute configuration.
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