Title: Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes.
Authors: Catalán, Luis Espinoza; Marín, Karen Catalán; Villegas, Alejandro Madrid; Altamirano, Héctor Carrasco; García, Joan Villena; Fritis, Mauricio Cuellar
Abstract: 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)-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 entlabdanes 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.
Subjects: HYDROQUINONE; DITERPENES; ANTINEOPLASTIC agents; METABOLITES; ALCOHOL; ORGANIC compounds; AROMATIC compounds; NUCLEAR magnetic resonance; PHOTOCHEMISTRY
Publication: Molecules, 2009, Vol 14, Issue 6, p2181
ISSN: 1420-3049
Publication type: Academic Journal
DOI: 10.3390/molecules14062181

Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes.

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