Total synthesis of (-)-mersicarpine
Nakajima, Ogino, Yokoshima, Fukuyama (2010) Total synthesis of (-)-mersicarpine J Am Chem Soc (IF: 14.4) 132(4) 1236-7Abstract
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.
Links
http://www.ncbi.nlm.nih.gov/pubmed/20055392http://dx.doi.org/10.1021/ja9103233
