he total synthesis of four naturally occurring dimeric stilbenes, (±)-shegansu B (1), gnetuhainin F (1a), (±)-maackin A (2) and (±)-cassigarol E (3), were studied. Isorhapontigenin (13) and piceatannol (14) were prepared from 3,5-dihydroxybenzoic acid in six steps. Oxidative coupling of 13 and 14 with HRP/H₂O₂ gave their respective dimeric compounds. The first total synthesis of 1a, (±)-2 and (±)-3 was described and the oxidative coupling yield of synthesis of (±)-1 was higher than that in literatures.

Key words: total synthesis, (±)-shegansu B, gnetuhainin F, (±)-maackin A, (±)-cassigarol E, HRP/H₂O₂, oxidative coupling