regioselective o-derivatization of quercetin via ester intermediates. an improved synthesis of rhamnetin and development of a new mitochondriotropic derivative槲皮素的特定选择的o-derivatization通过酯中间体。.pdfVIP

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regioselective o-derivatization of quercetin via ester intermediates. an improved synthesis of rhamnetin and development of a new mitochondriotropic derivative槲皮素的特定选择的o-derivatization通过酯中间体。.pdf

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regioselective o-derivatization of quercetin via ester intermediates. an improved synthesis of rhamnetin and development of a new mitochondriotropic derivative槲皮素的特定选择的o-derivatization通过酯中间体。

Molecules 2010, 15, 4722-4736; doi:10.3390/molecules OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Regioselective O-Derivatization of Quercetin via Ester Intermediates. An Improved Synthesis of Rhamnetin and Development of a New Mitochondriotropic Derivative 1 2 1 2 1 Andrea Mattarei , Lucia Biasutto , Federico Rastrelli , Spiridione Garbisa , Ester Marotta , Mario Zoratti 2,3 and Cristina Paradisi 1,* 1 Department of Chemical Sciences, Università di Padova, via Marzolo 1, 35131 Padova, Italy 2 Department of Biomedical Sciences, Università di Padova, viale G. Colombo 3, 35121 Padova, Italy 3 CNR Institute of Neuroscience, viale G. Colombo 3, 35121 Padova, Italy * Author to whom correspondence should be addressed; E-Mail: cristina.paradisi@unipd.it; Tel.: +39-049-827-5661; Fax: +39-049-827-5239. Received: 10 June 2010; in revised form: 22 June 2010 / Accepted: 2 July 2010 / Published: 6 July 2010 Abstract: 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 t