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Updated: Sep 9, 2025

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Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines
Alexander J Hughes1, Steven D Townsend1
1Department of Chemistry, Vanderbilt University, Nashville, TN 37235, United States.
Abstract:
We describe the first total syntheses of tabernanthine and ibogaline. Entry to these iboga alkaloid natural products is enabled by a thermal coupling of indoles and aziridines to furnish the requisite nosyl tryptamine starting materials. This route features a Friedel-Crafts type alkylation to form the key indole-isoquinuclidine C-C bond. Finally, a regio- and diastereoselective hydroboration-oxidation enables C-N bond formation to close the isoquinuclidine ring system and deliver tabernanthine and ibogaline in 10 and 14% yield respectively. Both syntheses were completed in eight steps.
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