Formation of an unusual dimeric compound by lead tetraacetate oxidation of a corynanthe-type indole alkaloid, mitragynine

Chem Pharm Bull (Tokyo). 2002 Jul;50(7):960-3. doi: 10.1248/cpb.50.960.

Abstract

Lead tetraacetate oxidation of a Corynanthe-type indole alkaloid, mitragynine, produced mainly 7-acetoxyindolenine derivative (2) together with a dimeric compound (4) as a minor product. The novel structure having a bridge between the C-11' and C-7 positions in the respective indolenine parts and its formation mechanism were studied.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anisoles
  • Chromatography, Thin Layer
  • Dimerization
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Organometallic Compounds / chemistry*
  • Oxidation-Reduction
  • Secologanin Tryptamine Alkaloids / chemistry*
  • Spectrophotometry, Ultraviolet

Substances

  • Anisoles
  • Indicators and Reagents
  • Organometallic Compounds
  • Secologanin Tryptamine Alkaloids
  • 1,3-dimethoxybenzene
  • lead tetraacetate
  • mitragynine