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

Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes

1,* , 1, 1, 2, 3 and 4
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 / Revised: 26 May 2009 / Accepted: 2 June 2009 / Published: 17 June 2009
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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 diterpenyl-hydroquinones; synthesis; ent-labdanes; NMR structural determination
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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