Molecules 2009, 14(6), 2181-2194; doi:10.3390/molecules14062181

Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes

1 Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile 2 Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N° 52, Viña del Mar, Chile 3 Facultad de Medicina, Universidad de Valparaíso, Centro Regional de Estudios en Alimentos Saludables, Creas, Av. Hontaneda N° 2664, Valparaíso, Chile 4 Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso, Chile
* Author to whom correspondence should be addressed.
Received: 10 May 2009; in revised form: 26 May 2009 / Accepted: 2 June 2009 / Published: 17 June 2009
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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)-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: diterpenyl-hydroquinones; synthesis; ent-labdanes; NMR structural determination

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MDPI and ACS Style

Catalán, L.E.; Marín, K.C.; Villegas, A.M.; Altamirano, H.C.; García, J.V.; Fritis, M.C. Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes. Molecules 2009, 14, 2181-2194.

AMA Style

Catalán LE, Marín KC, Villegas AM, Altamirano HC, García JV, Fritis MC. Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes. Molecules. 2009; 14(6):2181-2194.

Chicago/Turabian Style

Catalán, Luis Espinoza; Marín, Karen Catalán; Villegas, Alejandro Madrid; Altamirano, Héctor Carrasco; García, Joan Villena; Fritis, Mauricio Cuellar. 2009. "Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes." Molecules 14, no. 6: 2181-2194.

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