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Communication | Regular issue | Vol 3, No. 8, 1975, pp.639-649
Published online, 1st January, 1970
DOI: 10.3987/R-1975-08-0639
Studies on the Synthesis of Bisindole Alkaloids. II. The Synthesis of 3’,4’-Dehydrovinblastine, 4’-Deoxovinblastine and Related Analogues. The Biogenetic Approach

James P. Kutney,* Arnold H. Ratcliffe, Adi M. Treasurywala, and Stephen Wunderly

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

Abstract

A novel approach to the synthesis of bisindole alkaloids in the vinblastine series has been developed. This approach, which originates from biogenetic considerations is exemplified by the coupling of catharanthine and dihydrocatharanthine N-oxides with vindoline under Polonovski-type fragmentation conditions. The method which provides dimers with natural stereochemistry at C18, represents an exciting entry into this complex family from two readily available alkaloids.