Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines
European Journal of Organic Chemistry(2024)
摘要
We describe the first total synthesis 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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