Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes

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 Ar...

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Detalles Bibliográficos
Autores principales: Catalán, Luis Espinoza, Marín, Karen Catalán, Villegas, Alejandro Madrid, Altamirano, Héctor Carrasco, García, Joan Villena, Fritis, Mauricio Cuellar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2009
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254326/
https://www.ncbi.nlm.nih.gov/pubmed/19553891
http://dx.doi.org/10.3390/molecules14062181
Descripción
Sumario: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 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.

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