95763-99-8Relevant academic research and scientific papers
A Synthesis of Ibogamine
Kuehne, Martin E.,Reider, Paul J.
, p. 1464 - 1467 (1985)
A synthesis of ibogamine was developed by elaboration of 5-carbomethoxy-3-ethylcyclohexene.The latter was obtained as a 1:1 epimeric mixture from condensation of diethyl (2-ethyl-3-oxopropyl)malonate with triphenylvinylphosphonium bromide, followed by hydrolysis, decarboxylation, and esterification.
A Formal Synthesis of (+/-)-Ibogamine
Huffman, John W.,Shanmugasundaram, Giovindaswamy,Sawdaye, Reuben,Raveendranath, Panolil C.,Desai, Ranjit C.
, p. 1460 - 1464 (2007/10/02)
A formal synthesis of the indole alkaloid (+/-)-ibogamine (2) from a mixture of methyl cis- and trans-5-ethyl-3-cyclohexenecarboxylate is described.This mixture of esters was prepared by reaction of the lactone of 3-hydroxycyclohexenecarboxylic acid (14) with ethylmagnesium bromide-cuprous iodide-dimethyl sulfide to give, after esterification, trans ester 8.Epimerization gave a 3:2 mixture of esters 4 and 8, epoxidation of which, followed by reaction with tryptamine, gave an inseparable mixture of lactams 5 and 15.This mixture selectively afforded tosylate 3, a known synthetic precursor to (+/-)-ibogamine.Attempted preparation of esters 4 and 8 by elimination reactions of various derivatives of 2-ethyl-4-carboxycyclohexanone afforded mixtures containing significant amounts of methyl 3-ethyl-3-cyclohexenecarboxylate (10).
