4.3 Article

First Synthesis of Saponarin, 6-C- and 7-O-Di-β-D-glueosylapigenin

期刊

CHEMICAL & PHARMACEUTICAL BULLETIN
卷 61, 期 7, 页码 776-780

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PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c13-00264

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C,O-diglycosylflavone; regioselective deprotection; glycosylation; phloroacetophenone; hypoglycemic activity

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Saponarin, apigenin 6-C- and 7-O-bis-beta-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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