Total Synthesis of Resvebassianol A, a Metabolite of Resveratrol by .

Resveratrol is a well-known dietary polyphenol because it has a variety of beneficial biological activities. The fungus is one of the most frequently used microorganisms for the biotransformation of polyphenols. Recently, resvebassianol A (), a glycosylated metabolite of resveratrol by , was isolated and structurally elucidated. It was demonstrated to exhibit antioxidant, regenerative, and anti-inflammatory activities with no cytotoxicity. Here, we report the first total synthesis of resvebassianol A, 4'---(4‴--methylglucopyranosyl)resveratrol (), and its regiomer, 3---(4‴--methylglucopyranosyl)resveratrol (). Key reactions include (i) the construction of a stilbene core via a novel Heck reaction of aryl halides and styrenes, and (ii) glycosylation with unnatural methylglucopyranosyl bromide. The glycosylation step was carefully optimized by varying the bases and solvents. Resveratrol metabolites and were obtained at 7.5% and 6.3% of the overall yield, respectively.