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Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative

The regioselective synthesis of several quercetin (3,3’,4’,5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. Tetracetylated quercetin with the free OH on 7-C was selectively...

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Autores principales: Mattarei, Andrea, Biasutto, Lucia, Rastrelli, Federico, Garbisa, Spiridione, Marotta, Ester, Zoratti, Mario, Paradisi, Cristina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257647/
https://www.ncbi.nlm.nih.gov/pubmed/20657388
http://dx.doi.org/10.3390/molecules15074722
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author Mattarei, Andrea
Biasutto, Lucia
Rastrelli, Federico
Garbisa, Spiridione
Marotta, Ester
Zoratti, Mario
Paradisi, Cristina
author_facet Mattarei, Andrea
Biasutto, Lucia
Rastrelli, Federico
Garbisa, Spiridione
Marotta, Ester
Zoratti, Mario
Paradisi, Cristina
author_sort Mattarei, Andrea
collection PubMed
description The regioselective synthesis of several quercetin (3,3’,4’,5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. Tetracetylated quercetin with the free OH on 7-C was selectively obtained instead via imidazole-promoted deacylation of the corresponding pentaester. Unambiguous structural characterization of the two isomeric tetraacetyl quercetin derivatives was obtained by combined HSQC and HMBC 2D-NMR analysis. These molecules can be used as starting materials for the regioselective synthesis of other derivatives. High yield syntheses of the natural polyphenol rhamnetin (7-O-methylquercetin) and of the new mitochondriotropic compound 7-(4-triphenylphosphoniumbutyl) quercetin iodide are reported as examples.
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spelling pubmed-62576472018-12-06 Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative Mattarei, Andrea Biasutto, Lucia Rastrelli, Federico Garbisa, Spiridione Marotta, Ester Zoratti, Mario Paradisi, Cristina Molecules Article The regioselective synthesis of several quercetin (3,3’,4’,5,7-pentahydroxy flavone) tetraesters bearing a single free OH on 5-C was achieved in good yield by proper choice of reaction conditions using common esterification procedures. Tetracetylated quercetin with the free OH on 7-C was selectively obtained instead via imidazole-promoted deacylation of the corresponding pentaester. Unambiguous structural characterization of the two isomeric tetraacetyl quercetin derivatives was obtained by combined HSQC and HMBC 2D-NMR analysis. These molecules can be used as starting materials for the regioselective synthesis of other derivatives. High yield syntheses of the natural polyphenol rhamnetin (7-O-methylquercetin) and of the new mitochondriotropic compound 7-(4-triphenylphosphoniumbutyl) quercetin iodide are reported as examples. MDPI 2010-07-06 /pmc/articles/PMC6257647/ /pubmed/20657388 http://dx.doi.org/10.3390/molecules15074722 Text en © 2010 by the authors; http://creativecommons.org/licenses/by/3.0/ licensee MDPI, 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
Mattarei, Andrea
Biasutto, Lucia
Rastrelli, Federico
Garbisa, Spiridione
Marotta, Ester
Zoratti, Mario
Paradisi, Cristina
Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
title Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
title_full Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
title_fullStr Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
title_full_unstemmed Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
title_short Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative
title_sort regioselective o-derivatization of quercetin via ester intermediates. an improved synthesis of rhamnetin and development of a new mitochondriotropic derivative
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257647/
https://www.ncbi.nlm.nih.gov/pubmed/20657388
http://dx.doi.org/10.3390/molecules15074722
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