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■ Nucleophilic Substitution Reaction in Indole Chemistry: A Synthesis of Novel 7β-Substituted Yohimbine and 4aα-Substituted 1,2,3,4-Tetrahydro-β-carboline Derivatives

Katsumasa Yoshino, Fumio Yamada, and Masanori Somei*

*Faculty of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa, 920-1192, Japan

Abstract

X-Ray analyses of 1-hydroxyyohimbine derivatives clearly show the deviation of the N(1)-O bond from the indole molecular plane. This phenomenon supports our working hypothesis “bishomoallylic conjugation”. The deviation is responsible for the unprecedented nucleophilic substitution reaction in 1-hydroxyindole chemistry and effected the synthesis of novel 7β-heteroarylyohimbine and 4aα-heteroaryl-1,2,3,4-tetrahydro-β-carboline derivatives from the corresponding 1-hydroxyindole derivatives.