A general approach to 2,2-disubstituted indoxyls: total synthesis of brevianamide A and trigonoliimine C

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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 indoxylsvianucleophile 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 accessibleviaintramolecular nucleophilic trapping.

Original languageEnglish (US)
Pages (from-to)13756-13763
Number of pages8
JournalChemical Science
Volume12
Issue number41
DOIs
StatePublished - Nov 7 2021

ASJC Scopus subject areas

  • Chemistry(all)

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