Next Article in Journal
Determination of the Volatile Composition of Rhodobryum giganteum (Schwaegr.) Par. (Bryaceae) Using Solid-phase Microextraction and Gas Chromatography/Mass Spectrometry (GC/MS)
Previous Article in Journal
Effect of Extraction Solvent/Technique on the Antioxidant Activity of Selected Medicinal Plant Extracts
Article Menu

Export Article

Open AccessArticle
Molecules 2009, 14(6), 2181-2194;

Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes

Departamento de Química, Universidad Técnica Federico Santa María, Av. España N° 1680, Valparaíso, Chile
Departamento de Ciencias Químicas, Universidad Andrés Bello, Campus Viña del Mar, Los Fresnos N° 52, Viña del Mar, Chile
Facultad de Medicina, Universidad de Valparaíso, Centro Regional de Estudios en Alimentos Saludables, Creas, Av. Hontaneda N° 2664, Valparaíso, Chile
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
Full-Text   |   PDF [494 KB, uploaded 18 June 2014]   |  


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. View Full-Text
Keywords: diterpenyl-hydroquinones; synthesis; ent-labdanes; NMR structural determination diterpenyl-hydroquinones; synthesis; ent-labdanes; NMR structural determination

Graphical abstract

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics



[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top