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

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines ; day:22 ; month:05 ; year:2024 ; extent:5
European journal of organic chemistry ; (22.05.2024) (gesamt 5)

Creator: Hughes, Alexander J.
Townsend, Steven D.

DOI: 10.1002/ejoc.202400442

URN: urn:nbn:de:101:1-2405231408108.645346213284

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:52 AM CEST

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Hughes, Alexander J.
Townsend, Steven D.

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

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