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.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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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)
- Urheber
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Hughes, Alexander J.
Townsend, Steven D.
- DOI
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10.1002/ejoc.202400442
- URN
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urn:nbn:de:101:1-2405231408108.645346213284
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 10:52 MESZ
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Beteiligte
- Hughes, Alexander J.
- Townsend, Steven D.
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