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Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines.

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.

SUBMITTER: Hughes AJ 

PROVIDER: S-EPMC12392802 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature

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Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines.

Hughes Alexander J AJ   Townsend Steven D SD  

European journal of organic chemistry 20240426 30

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 a  ...[more]

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