Total Synthesis of Two Isoflavone Bis-C-glycosides: Genistein and Orobol 6,8-Di-C-β-D-glucopyranosides

This paper describes the first successful synthesis of two isoflavone bis-C-glycosides, genistein and orobol 6,8-di-C-beta-D-glucopyranosides from phloroacetophenone bis-C-glycoside in total yields of 27 and 19%, respectively, using a four-step reaction: direct C-glycosylation of phloroacetophenone with unprotected D-glucose; chalcone synthesis by aldol condensation; acetal synthesis by oxidative rearrangement using DIB and p-TsOH; and formation of the isoflavone ring using HCl, without protection of the glucose moiety.