Efficient Synthesis of Flavanone Glucuronides

The first efficient synthesis of flavanone glucuronides as potential human metabolites is described. The synthetic strategy is based on acetyl protection, followed by a combination of chemical and enzymatic deprotection steps. As an example, the method is applied to a synthesis of 7,4'-di-O-methyleriodictyol 3'-O-beta-D-glucuronide. The aglycone is a flavanone naturally present in tarragon spice (Artemisia dracunculus) as well as in various Chinese, Brazilian, and Malaysian medicinal plants.