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■ Cleavage of the C-20 Ethylidene Side-Chain of Deformyl-Z- and Deformyl-E-geissoschizine Derivatives Utilizing the Modified Polonovski Reaction

Mauri Lounasmaa,* Reija Jokela, Minna Halonen, and Jari Miettinen

*Laboratory for Organic and Bioorganic Chemistry, Technical University of Helsinki, P.O. Box 6100, SF-02150 HUT Espoo, Finland

Abstract

Cleavage of the C-20 ethylidene side-chain of deformyl-Z-geissoschizine (1) and deformyl-E-geissoschizine (2), and their N_a-Boc derivatives (11) and (12), utilizing the modified Polonovski reaction, is described. Mechanistic considerations are presented.