Total Synthesis of Two Glycosylated Stilbenes, Oxyresveratrol 2-O-β-D-Glucopyranoside and 2,3,5,4′-Tetrahydroxystilbene 2-O-β-D-Glucopyranoside

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-beta-D-glucopyranoside (1) and 2,3,5,4'-tetrahydroxystilbene 2-O-beta-D-glucopyranoside (19, 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.