Regioselective Oxidative Coupling of 4-hydroxystilbenes: Synthesis of Resveratrol and Epsilon-viniferin (E)-dehydrodimers

Treatment of 5-[2-(4-hydroxyphenyl)vinyl]benzene-1,3-diol (resveratrol) with an equimolar amount of silver(I) acetate in dry MeOH at 50 degrees C for 1 h followed by chromatographic purification with a short silica gel column allowed the isolation of its (E)-dehydrodimer, 5-[5-[2-(3,5-dihydroxyphenyl)vinyl]-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-3-yl]benzene-1,3-diol, as a racemic mixture in high yield. The present method was applicable to the oxidative dimerization of 4-hydroxystilbenes such as trans-styrylphenol and 5-[6-hydroxy-2-(4-hydroxyphenyl)-4-[2-(4-hydroxyphenyl)vinyl]-2,3-dihydrobenzofuran-3-yl]benzene-1,3-diol (epsilon-viniferin) leading to the corresponding 2-(4-hydroxyphenyl)-2,3-dihydrobenzofurans possessing various types of biological activities.