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Communication | Regular issue | Vol 4, No. 5, 1976, pp.997-1005
Published online, 1st January, 1970
DOI: 10.3987/R-1976-05-0997
Studies on the Sythesis of Bisindole Alkaloids. III. The Synthesis of Leurosine and 3’-Hydroxyvinblastine

James P. Kutney,* John Balsevich, Gordon H. Bokelman, Toshihiko Hibino, Isamu Itoh, and Arnold H. Ratcliffe

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


An interesting reaction which allows direct functionalization of the 3,4-double bond in the cleavamine series has been developed. Application of this reaction to the previously synthesized 3’,4’-dehydrovinblastine (VIII, R = CO2CH3) allows a direct synthesis of the dimeric Vinca alkaloid leurosine (IX, R = CO2CH3).
In another series of investigations directed at functionalizing the 3’,4’-double band of VIII (R = CO2CH3) osmylation of the N-oxide intermediate of the latter has allowed the synthesis of 3’-hydroxyvinblastine (XI, R = CO2CH3), a close relative of the alkaloid vincadioline.