Molecules

Regioselective O-derivatization of quercetin via ester intermediates. An improved synthesis of rhamnetin and development of a new mitochondriotropic derivative

A Mattarei, L Biasutto, F Rastrelli, S Garbisa, E Marotta…

Index: Mattarei, Andrea; Biasutto, Lucia; Rastrelli, Federico; Garbisa, Spiridione; Marotta, Ester; Zoratti, Mario; Paradisi, Cristina Molecules, 2010 , vol. 15, # 7 p. 4722 - 4736

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Citation Number: 21

Abstract

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 ...