Abstract

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