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First synthesis of saponarin, 6-C- and 7-O-di-β-D-glucosylapigenin
Kazufumi Misawa1, Yasuko Takahashi, Shingo Sato
1Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata 992–8510, Japan.
Abstract:
Saponarin, apigenin 6-C- and 7-O-bis-β-D-glucoside, was synthesized in an overall yield of 37% via 11 steps, which included the C-glycosylation of 2,4-O-dibenzylphloroacetophenone, the introduction of a cinnamoyl residue by aldol condensation, the formation of a flavone by regioselective deprotection, and oxidative ring-closure to the final regioselective deprotection and stereoselective O-glycosylation.
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