Abstract
Quercetin, the polyphenolic compound, which has the highest daily intake, is well known for its protective effects against aging diseases and has received a lot of attention for this reason. Both quercetin 3- O-β- d-glucuronide and quercetin 3′- O-β- d-glucuronide are human metabolites, which, together with their regioisomers, are required for biological as well as physical chemistry studies. We present here a novel synthetic route based on the sequential and selective protections of the hydroxyl functions of quercetin allowing selective glycosylation, followed by TEMPO-mediated oxidation to the glucuronide. This methodology enabled us to synthesize the five O-β- d-glucosides and four O-β- d-glucuronides of quercetin, including the major human metabolite, quercetin 3- O-β- d-glucuronide.
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