Synthesis of two new hemisynthetic diterpenylhydroquinones from natural ent-labdanes.
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.
Catalán
Luis Espinoza
LE
Departamento de Química, Universidad Técnica Federico Santa María, Av. España N degrees 1680, Valparaíso, Chile. luis.espinozac@usm.cl
Marín
Karen Catalán
KC
Villegas
Alejandro Madrid
AM
Altamirano
Héctor Carrasco
HC
García
Joan Villena
JV
Fritis
Mauricio Cuellar
MC
D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
D004224:Diterpenes; D006873:Hydroquinones