Synthesis of two new hemisynthetic diterpenylhydroquinones from natural ent-labdanes

Molecules. 2009 Jun 17;14(6):2181-94. doi: 10.3390/molecules14062181.

Abstract

The synthesis and structural determination of two new diterpenylhydroquinones: 2beta-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2beta-hydroxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-dieneis reported (2). These compounds were obtained by coupling via Electrophilic Aromatic Substitution (EAS) of 1,4-hydroquinone with primary or tertiary allyl alcohol derivatives of the natural ent-labdanes 3 and 4. With this new method, the best results were observed when mixtures of the primary alcohol derivatives 5-6 (26% yield of compound 1) and diol derivatives 9-10 (28% yield of compound 2) were used.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemical synthesis*
  • Diterpenes / chemistry*
  • Hydroquinones / chemical synthesis*
  • Hydroquinones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Diterpenes
  • Hydroquinones