{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Hughes AJ"],"funding":["NIGMS NIH HHS"],"pagination":["e202400442"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC12392802"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["27(30)"],"pubmed_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."],"journal":["European journal of organic chemistry"],"pubmed_title":["Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines."],"pmcid":["PMC12392802"],"funding_grant_id":["R35 GM133602"],"pubmed_authors":["Townsend SD","Hughes AJ"],"additional_accession":[]},"is_claimable":false,"name":"Total Synthesis of Tabernanthine and Ibogaline: Rapid Access to Nosyl Tryptamines.","description":"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.","dates":{"release":"2024-01-01T00:00:00Z","publication":"2024 Aug","modification":"2026-05-29T21:31:50.199Z","creation":"2026-04-08T06:05:58.452Z"},"accession":"S-EPMC12392802","cross_references":{"pubmed":["40896447"],"doi":["10.1002/ejoc.202400442"]}}