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Communication | Regular issue | Vol 3, No. 3, 1975, pp.205-212
Published online, 1st January, 1970
DOI: 10.3987/R-1975-03-0205
■ Studies on the Synthesis of Bisindole Alkaloids. The Synthesis, Structure and Absolute Configuration of 18’-Epi-4’-deoxo-4’-epivinblastine, 18’-Decarbomethoxy-18’-epi-4’-epivinblastine and 18’-Epi-3’,4’-dehydrovinblastine

James P. Kutney,* James Cook, Kaoru Fuji, Adi M. Treasurywala, Jon Clardy, Jose Fayos, and Hal Wright

*Department of Chemisry, University of British Columbia, Vancouver 8, V5T 1W5, Canada

Abstract

Studies on the syntheses of 18’-epi-4’-deoxo-4’-epivinblastine (III), 18’-epi-3’,4’-dehydrovinblastine (III, 3’,4’-double bond) and 18’-decarbomethoxy-l8’-epi-4’-deaxo-4’-epivinblastine (V) are described. Particular emphasis is placed on the stereochemistry of the coupling reaction involving chloroindolenine derivatives of the cleavamine series with vindoline under acidic conditions. X-ray analyses on III and V provide the complete structures, including absolute configuration. These studies reveal that the chloroindolenine approach provides products bearing the unnatural configuration at C18’.