Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization

Sci Rep. 2021 Oct 7;11(1):19915. doi: 10.1038/s41598-021-99064-8.

Abstract

The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Cyclization
  • Indole Alkaloids / chemical synthesis*
  • Indole Alkaloids / chemistry
  • Molecular Structure
  • Naphthols / chemistry*
  • Oxidation-Reduction*
  • Phosphoric Acids / chemistry*

Substances

  • BINOL, naphthol
  • Indole Alkaloids
  • Naphthols
  • Phosphoric Acids
  • decursivine
  • phosphoric acid