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Communication | Regular issue | Vol 6, No. 2, 1977, pp.129-135
Published online, 1st January, 1970
DOI: 10.3987/R-1977-02-0129
A New Stereoselective Synthesis of (±)-Deoxyaspidodispermine

Yasushi Honma and Yoshio Ban*

*Faculty of Pharmaceutical Sciences, Toho University, 2-2-1, Miyama, Funabashi, Chiba 274-8510, Japan

Abstract

A new stereoselective total synthesis of (±)-deoxyaspidodispermine (I) was achieved; the feature of the present synthesis was to involve the photosensitized oxygenation of the diene (V) by singlet oxygen, exclusively furnishing the cyclic peroxide adduct (VI) of 6-orientation, which might be regarded as a biomimetic process subsequent to Djerassi’s work on the removal of the angular ethyl group of Aspidosperma alkaloids.