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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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
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author Catalán, Luis Espinoza
Marín, Karen Catalán
Villegas, Alejandro Madrid
Altamirano, Héctor Carrasco
García, Joan Villena
Fritis, Mauricio Cuellar
author_facet Catalán, Luis Espinoza
Marín, Karen Catalán
Villegas, Alejandro Madrid
Altamirano, Héctor Carrasco
García, Joan Villena
Fritis, Mauricio Cuellar
author_sort Catalán, Luis Espinoza
collection PubMed
description 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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spelling pubmed-62543262018-11-30 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 Molecules Article 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. Molecular Diversity Preservation International 2009-06-17 /pmc/articles/PMC6254326/ /pubmed/19553891 http://dx.doi.org/10.3390/molecules14062181 Text en © 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Catalán, Luis Espinoza
Marín, Karen Catalán
Villegas, Alejandro Madrid
Altamirano, Héctor Carrasco
García, Joan Villena
Fritis, Mauricio Cuellar
Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
title Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
title_full Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
title_fullStr Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
title_full_unstemmed Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
title_short Synthesis of Two New Hemisynthetic Diterpenylhydroquinones from Natural Ent-Labdanes
title_sort synthesis of two new hemisynthetic diterpenylhydroquinones from natural ent-labdanes
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6254326/
https://www.ncbi.nlm.nih.gov/pubmed/19553891
http://dx.doi.org/10.3390/molecules14062181
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