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Communication | Special issue | Vol 5, No. 1, 1976, pp.267-273
Published online, 1st January, 1970
DOI: 10.3987/S-1976-01-0267
Introduction of Substituents to C3 of Yohimbinoid Skeleton

Norio Aimi,* Yoshihisa Asada, Shizuko Tsuge, Teruo Kohmoto, Kin’ichi Mogi, and Shin-ichiro Sakai

*Faculty of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

Chlorination took place at the nucleophilic centres of tabersonine (1) and yohimbine (4) when their hydrochlorides were oxidized with m-chloro perbenzoic acid. Chloroindolenine N-oxide (5), thus obtained from yohimbine, was susceptible to nucleophilic attack at C3 position to give stable 3-substituted yohimbine Nb-oxides. No indication of the rearrangement to oxindole was observed.