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Communication | Regular issue | Vol 27, No. 8, 1988, pp.1845-1853
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4611
■ A Highly Efficient and Commercially Important Synthesis of the Antitumor Catharanthus Alkaloids Vinblastine and Leurosidine from Catharanthine and Vindoline

James Peter Kutney,* Lewis Siu Leung Choi, Jun Nakano, Hiroki Tsukamoto, Michael McHugh, and Camille Andre Boulet

*Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, B.C., V6T 1Z1, Canada

Abstract

Extensive studies of various reaction parameters for the chemical coupling of catharanthine (1) and vindoline (2) followed by evaluation of highly unstable intermediates by careful reaction control have provided essentially a quantitative yiald in this coupling reaction. Subsequent regioselective reduction of the resultant intermediate 3 by select NADH models affords. a high yield of an enamins (5) which, without isolation, is selectively oxidized to unstable iminium intermediates 6 and 7 and the latter, again without isolation. are finally reduced to vinblastins (8,40%), leurosidine (10,16%), and 3’,4’-enhydrovinblastine (4,12%). The entire process of five steps (1→11+2→3→5→6,7→8,10,4) can be achieved in a one-pot operation and the high overall yield of vinblastine (8) requires that each reaction must proceed in yields in excess of 80%.