Total synthesis of optically active chanoclavine-I

Article abstract of DOI:10.1016/S0040-4039(97)82950-4

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 tetrahydrobenz[c,d]indole derivative (7), in high yield.