A mild and convenient procedure for the conversion of toxic beta-asarone into rare phenylpropanoids: 2,4,5-trimethoxycinnamaldehyde and gamma-asarone

J Nat Prod. 2002 May;65(5):764-5. doi: 10.1021/np010559s.

Abstract

Oxidation of beta-asarone (2) with DDQ gave trans-2,4,5-trimethoxycinnamaldehyde (3), which on treatment with p-toluenesulfonyl hydrazine provided corresponding alpha,beta-unsaturated hydrazone derivative (4). Reduction of 4 with sodium borohydride in acetic acid afforded gamma-asarone (1) in 43% yield.

MeSH terms

  • Acorus / chemistry*
  • Acrolein / analogs & derivatives
  • Acrolein / chemistry*
  • Allylbenzene Derivatives
  • Anisoles / chemistry*
  • Catalysis
  • Chemistry, Organic / methods
  • Chromatography, Thin Layer
  • Hydrazones / chemistry*
  • India
  • Nuclear Magnetic Resonance, Biomolecular
  • Oxidation-Reduction
  • Plants, Medicinal / chemistry*
  • Rhizome / chemistry
  • Stereoisomerism
  • Toxins, Biological / chemistry

Substances

  • 2,4,5-trimethoxycinnamaldehyde
  • 2,4,5-trimethoxycinnamyltosylhydrazone
  • Allylbenzene Derivatives
  • Anisoles
  • Hydrazones
  • Toxins, Biological
  • asarone
  • Acrolein