Molecules (Jun 2009)

Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes

  • Mauricio Cuellar Fritis,
  • Joan Villena García,
  • Luis Espinoza Catalán,
  • Héctor Carrasco Altamirano,
  • Alejandro Madrid Villegas,
  • Karen Catalán Marín

DOI
https://doi.org/10.3390/molecules14062181
Journal volume & issue
Vol. 14, no. 6
pp. 2181 – 2194

Abstract

Read online

The synthesis and structural determination of two new diterpenylhydroquinones: 2β-acetoxy-15-phenyl-(22,25-dihydroxy)-ent-labda-8(17),13(E)-diene(1) and 2β-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.

Keywords