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Report | Regular issue | Vol 19, No. 10, 1982, pp.1883-1888
Published online, 1st January, 1970
DOI: 10.3987/R-1982-10-1883
The Absolute Configuration of Stephanine and Crebanine

Jun-ichi Kunitomo, Miyoko Satoh, Yasuo Watanabe, Matao Matsui, Masatoshi Inoue, and Toshimasa Ishida

*Faculty of Pharmaceutical Science, Mukogawa-Women’s University, 11-68 Koushien Kyuban-Cho, Nishinomiya, Hyogo 663-8179, Japan

Abstract

The crystal structure of natural stephanine (1) has been determined by X-ray diffraction. The C-6a position was confirmed to be of the R-configuration. O-Methyl derivatives of the products by cleavage reaction with sodium in liquid ammonia of stephanine (1) and crebanine (2) were both identified as 2,8-dimethoxyaporphine (3). This showed that crebanine (2) was of the R-configuration which has also been reported based on CD data. This work yielded the exact configuration at C-6a far all known aporphine-type alkaloids.