M. Sako, Hiroyuki Hosokawa, Tetsuro Ito
Mar 2, 2004
Citations
2
Influential Citations
81
Citations
Quality indicators
Journal
Journal of Organic Chemistry
Abstract
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 °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 (e-viniferin) leading to the corresponding 2-(4-hydroxyphenyl)-2,3-dihydrobenzofurans possessing various types of biological activities.