Chemical Transformations of Ibogaine

Abstract

Ibogaine has been converted to the naturally occuring ester alkaloid voacangine by a four-step sequence. Treatment of ibogaine with t-butyl hypochlorite yielded the chloroindolenine which combined with potassium cyanide to give 18-cyanoibogaine and an isomeric nitrile resulting from an amusing rearrangement. Vigorous base hydrolysis of the former nitrile followed by esterification with diazomethane furnished voacangine. The chloroindolenine served also as a convenient intermediate for the preparation of 18-methoxy- and 18-hydroxyibogaine.

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