Total synthesis of apigenin-4'-yl 2-O-(p-coumaroyl)-β-D-glucopyranoside.

The first total synthesis of apigenin-4'-yl 2-O-(p-coumaroyl)-β-D-glucopyranoside, which exhibits good inhibitory activity against xanthine oxidase (XO), was accomplished in seven steps from a 1,2-blocked sugar unit and natural apigenin. A unique allyl protecting group, a phase-transfer-catalyzed (PTC) regioselective coupling reaction, and robustness in large-scale preparation are the merits of this synthetic strategy.