biostudies-literatureHughes AJNIGMS NIH HHSe202400442https://www.ebi.ac.uk/biostudies/studies/S-EPMC12392802biostudies-literatureUnknown27(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 and ibogaline in 10 and 14% yield respectively. Both syntheses were completed in eight steps.European journal of organic chemistryTotal Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines.PMC12392802R35 GM133602Townsend SDHughes AJfalseTotal Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines.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.2024-01-01T00:00:00Z2024 Aug2026-05-29T21:31:50.199Z2026-04-08T06:05:58.452ZS-EPMC123928024089644710.1002/ejoc.202400442