Unified Strategyfor the Concise Total Syntheses ofAll Six 3″‑<i>O</i>‑Acyl QuercitrinsBased on Regioselective Acylation Catalyzed by Boronic Acid

The naturally occurring 3″-<i>O</i>-acylquercitrin family exhibits a range of biological activities with significant potential health and medical benefits. Herein, we present a unified strategy for concise total syntheses of all six known 3″-<i>O</i>-acylquercitrin natural productsnamely, 3″-<i>O</i>-galloylquercitrin, 3″-<i>O</i>-(<i>E</i>)-cinnamoylquercitrin, 3″-<i>O</i>-(<i>E</i>)-coumaroylquercitrin, 3″-<i>O</i>-(<i>E</i>)-feruloylquercitrin, 3″-<i>O</i>-acetylquercitrin, and 3″-<i>O</i>-tigloylquercitrinbased on regioselective acylation of carbohydrates catalyzed by <i>N</i>-methylimidazole-containing boronic acid. The core advancement in this approach is a late-stage catalytic regioselective functionalization of a common synthetic intermediate, enabling efficient access to the natural products.