Attempt to Synthesize 2,3,5,4′-Tetrahydroxystilbene Derived from 2,3,5,4′-Tetrahydroxystilbene-2-O-β-glucoside (THSG)

Masafumi Tamura; Yuhei Koshibe; Kiho Kaji; Jun-ya Ueda; Yoshiaki Shirataki

doi:10.1248/cpb.c14-00626

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Attempt to Synthesize 2,3,5,4′-Tetrahydroxystilbene Derived from 2,3,5,4′-Tetrahydroxystilbene-2-O-β-glucoside (THSG)

Masafumi Tamura , Yuhei Koshibe, Kiho Kaji, Jun-ya Ueda, Yoshiaki Shirataki

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Keywords: Polygonum multiflorum, Mizoroki–Heck reaction, 2-aryl-2,3-dihydrobenzofuran, 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG)

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2015 Volume 63 Issue 2 Pages 122-125

DOI https://doi.org/10.1248/cpb.c14-00626

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Abstract

An attempt to synthesize aglycone 1 derived from 2,3,5,4′-tetrahydroxystilbene-2-O-β-glucoside (THSG) via the Wittig reaction and Mizoroki–Heck reaction is described. In the Wittig protocol, 2,3,5,4′-tetramethoxystilbene 2 was obtained. Additionally, a palladium-catalyzed Mizoroki–Heck reaction strategy yielded 2-aryl-2,3-dihydrobenzofuran 13 instead of derivative 12 in good yield.

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