Synthesis of totarane diterpenes: totarol, maytenoquinone, 6-deoxymaytenoquinone and 8,11,13-totaratriene-12,13-diol

Chem Pharm Bull (Tokyo). 2008 Mar;56(3):287-91. doi: 10.1248/cpb.56.287.

Abstract

The syntheses of four totarane diterpenes-totarol, 8,11,13-totaratriene-12,13-diol, 6-deoxymaytenoquinone and maytenoquinone-are described. Totarol was synthesized via cyclization of a modified polyene. 8,11,13-Totaratriene-12,13-diol was prepared from natural totarol by ortho-oxidation with mCBPO (m-chlorobenzoyl peroxide). Maytenoquinone and 6-deoxymaytenoquinone were synthesized from 8,11,13-totaratriene-12,13-diol. 1H-NMR analysis showed that tautomeric isomerization between 6-deoxymaytenoquinone (2-hydroxy-4-quinone methide) and the ortho-quinone was very slow.

MeSH terms

  • Abietanes
  • Alkylation
  • Anti-Infective Agents / chemistry*
  • Chromatography, Thin Layer
  • Cyclization
  • Diterpenes / chemistry*
  • Harpagophytum / chemistry
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Conformation
  • Oxidation-Reduction
  • Spectrophotometry, Infrared

Substances

  • 6-deoxymaytenoquinone
  • 8,11,13-totaratriene-12,13-diol
  • Abietanes
  • Anti-Infective Agents
  • Diterpenes
  • Indicators and Reagents
  • maytenoquinone
  • totarol