ArticleEuropean journal of organic chemistry2024
Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines.
Article in European journal of organic chemistry, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.
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Who cites it
3 citing papers in PubMed.
- Discovery of Iboga-Derived Ligands for the Sigma‑2 Receptor.ACS bio & med chem Au · 2025Article
- Mechanism and Origin of Regioselectivity in the Phosphine-Catalyzed Heine Reaction.The Journal of organic chemistry · 2025Article
- Efficient and modular synthesis of ibogaine and related alkaloids.Nature chemistry · 2025Article
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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.
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