Total synthesis of (-)-mersicarpine.
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.
Nakajima
Rie
R
Graduate School of Pharmaceutical Sciences, University of Tokyo,7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Ogino
Tsuyoshi
T
Yokoshima
Satoshi
S
Fukuyama
Tohru
T
D002384:Catalysis; D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
D026121:Indole Alkaloids; C529544:mersicarpine