{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Xu F"],"funding":["University of Texas Southwestern Medical Center","Welch Foundation"],"pagination":["13756-13763"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8549782"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["12(41)"],"pubmed_abstract":["The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds. Here, we report a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxyls <i>via</i> nucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps). The developed method is operationally simple and demonstrates broad scope in terms of nucleophile identity and indole substitution, tolerating 2-alkyl substituents and free indole N-H groups, elements beyond the scope of most prior approaches. Spirocyclic indoxyl products are also accessible <i>via</i> intramolecular nucleophilic trapping."],"journal":["Chemical science"],"pubmed_title":["A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C."],"pmcid":["PMC8549782"],"funding_grant_id":["I-2045"],"pubmed_authors":["Xu F","Smith MW"],"additional_accession":[]},"is_claimable":false,"name":"A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C.","description":"The indoxyl unit is a common structural motif in alkaloid natural products and bioactive compounds. Here, we report a general method that transforms readily available 2-substituted indoles into 2,2-disubstituted indoxyls <i>via</i> nucleophile coupling with a 2-alkoxyindoxyl intermediate and showcase its utility in short total syntheses of the alkaloids brevianamide A (7 steps) and trigonoliimine C (6 steps). The developed method is operationally simple and demonstrates broad scope in terms of nucleophile identity and indole substitution, tolerating 2-alkyl substituents and free indole N-H groups, elements beyond the scope of most prior approaches. Spirocyclic indoxyl products are also accessible <i>via</i> intramolecular nucleophilic trapping.","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Oct","modification":"2026-05-09T10:01:22.944Z","creation":"2022-02-11T12:42:18.761Z"},"accession":"S-EPMC8549782","cross_references":{"pubmed":["34760160"],"doi":["10.1039/d1sc03533a"]}}