Abbreviated Ibogaine Congeners. Synthesis and Reactions of Tropan-3-yl-2- and -3-indoles. Investigation of an Unusual Isomerization of 2-Substituted Indoles Using Computational and Spectroscopic Techniques
The Journal of Organic Chemistry April 1, 1994 David B. Repke, Dean R. Artis, Janis T. Nelson et al. 40 citations
The synthesis and reactions of tropan-3-yl-2- and -3-indoles, abbreviated congeners of the psychoactive alkaloid ibogaine, are described. An unusual isomerization of 2-substituted indoles was investigated using computational and spectroscopic techniques. The work provides synthetic routes to these compounds and characterizes the isomerization process, contributing to the chemistry of axial and atropisomeric chirality in alkaloid synthesis.