ChemInform Abstract: A Novel Approach to Iboga Alkaloids: Total Synthesis of (.+-.)- Ibogamine and (.+-.)-epi-Ibogamine.
Abstract
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ChemInform Abstract
The procedure for the synthesis of the title alkaloids starts with the electrophilic substitution at C2 of the tryptamine derivative (II) by the allylic compound (I). The resulting adduct (III) is elaborated to the diastereomeric azepines (VI) and (VII). Finally, neat thermolysis of the minor isomer (VII) followed by hydride reduction yields the desired (.+-.)-ibogamine (IX). The corresponding epi-derivative can be obtained from (VI) by a similar procedure.
