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

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Andrea MattareiCristina Paradisi

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 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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Citations

Mar 22, 2012·Biochimica Et Biophysica Acta·Nicola SassiMario Zoratti
Aug 30, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Sunhwa ParkJae Hong Seo
Feb 10, 2017·Journal of Agricultural and Food Chemistry·Luís CruzNuno Mateus
Jul 22, 2017·Pharmacological Research : the Official Journal of the Italian Pharmacological Society·Nicola SassiLucia Biasutto
Feb 9, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Silvia Laura Guzmán-GutiérrezRicardo Reyes-Chilpa
Oct 28, 2017·Future Medicinal Chemistry·Domenico IacopettaMaria Stefania Sinicropi
Jul 25, 2019·Chemical Communications : Chem Comm·Giorgia Del FaveroChristian F W Becker
Nov 19, 2019·International Journal of Radiation Biology·Prabha Tiwari, Kaushala Prasad Mishra
Mar 11, 2019·ACS Biomaterials Science & Engineering·Sathyasivam KaviarasiUma Maheswari Krishnan

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Methods Mentioned

BETA
acylation
NMR
deacylation

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