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The first total synthesis of optically active costaclavine (18), an ergot alkaloid, was accomplished starting from methyl [4R-(Z)]-[4-[[(1, 1-dimethylethoxy)carbonyl]methylamino]-3, 4-dihydro-1-[(4-methylphenyl)sulfonyl]-benz[cd]indol-5(1H)-ylidene]acetate (8), which was prepared by intramolecular cyclization of 1, 1-dimethylethyl[1R-(E)]-[1-[[4-bromo-1-[(4-methylphenyl)-sulfonyl]-1H-indol-3-yl]methyl]-4-carbomethoxy-2-propenyl]methylcarbamate (7) according to the method we developed earlier during the course of the total synthesis of chanoclavine-I (9).

Total Synthesis of Optically Active Costaclavine. Synthetic Studies of Indoles and Related Compounds. Part 48.