Total synthesis of optically active chanoclavine-I

The total synthesis of optically active chanoclavine-I, an ergot alkaloid, was accomplished using palladium-catalyzed intramolecular cyclization (Heck reaction) as a key step. The conjugate ester (6) was obtained in 2 steps from optically active 4-bromotryptophan (10), and the cyclization of 6 proceeded smoothly without racemization to give the key intermediate, tricyclic tetrahydrobenzc,d]indole derivative (7), in high yield.