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Communication | Regular issue | Vol 3, No. 3, 1975, pp.197-204
Published online, 1st January, 1970
DOI: 10.3987/R-1975-03-0197
The Total Synthesis of Akuammicine and 16-Epi-stemmadenine. The Absolute Configuration of Stemmademine

James P. Kutney* and George B. Fuller

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

Abstract

A synthetic route leading to akuammicine (VI) and 16-epi-stemmadenine (XI) is presented. The synthesis employs Wieland-Gumlich aldehyde (III), a well-known degradation product of strych-nine (II), as a starting material. Introduction of functionality at C16 in the intermediate VIIl is done in a stereochemically unambiguous fashion thereby allowing direct comparison of the synthetic substances with the natural stemmadenine series. In this manner the complete absolute configuration of stemmadenine (I) is derived.