Glycosylated stilbenes are biologically active secondary metabolites of plants and have the potential to alleviate a broad range of human diseases. However, some of these compounds are not naturally abundant, and thus the synthesis of such molecules is desirable. This paper reports the first synthesis of oxyresveratrol 2-O-β-d-glucopyranoside (1) and 2,3,5,4′-tetrahydroxystilbene 2-O-β-d-glucopyranoside (1′), which are stilbene glycosides obtained from the rhizomes of Schoenocaulon officinale and Polygonum multiflorum, respectively. A facile four-step synthesis of 1 involved selective protection of the hydroxy groups and Wittig olefination to generate the compound in 8% overall yield. For compound 1′, a 10-step synthesis utilized selective protection of the hydroxy groups, Baeyer–Villiger oxidation, modified Duff formylation, and Wittig olefination to generate the compound in 6.9% overall yield.

中文翻译：

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两种糖基化对苯二酚的合成：氧白藜芦醇2 - O -β-d-葡糖苷和2,3,5,4'-四羟基sti2- O -β-d-葡糖苷

糖基化的对苯二酚是植物的生物活性次生代谢产物，具有缓解广泛人类疾病的潜力。然而，这些化合物中的一些不是天然丰富的，因此期望合成此类分子。本文报道了氧白藜芦醇2- O- β- d-吡喃葡萄糖苷（1）和2,3,5,4'-四羟基sti -2- （2 - O - β - d-吡喃葡萄糖苷（1'）的首次合成，这是一种二苯乙烯苷分别来自Schoenocaulon officinale和何首乌的根茎。轻松的四步合成1涉及羟基的选择性保护和Wittig烯化反应以8％的总收率生成该化合物。对于化合物1'，分十步进行的合成利用了羟基的选择性保护，Baeyer-Villiger氧化，改良的Duff甲酰化和Wittig烯烃化，以6.9％的总收率生成该化合物。