An effective synthesis of isoorientin: the regioselective synthesis of a 6-C-glucosylflavone

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• 作者：Kumazawa ; Toshihiro ; Minatogawa ; Tomomi ; Matsuba ; Shigeru ; Sato ; Shingo ; Onodera ; Jun-ichi
• 关键词：Isoorientin ; 6-C-Glycosyl flavone ; C-Glycosyl compound ; 2-Methylbenzyl group ; Hydrogenolysis
• 刊名：Carbohydrate Research
• 出版年：2000
• 出版时间：November 17, 2000
• 年：2000
• 卷：329
• 期：3
• 页码：507-513
• 全文大小：117 K

文摘

Isoorientin, a 6-C-β-d-glucopyranosyl-3′,4′,5,7-tetrahydroxyflavone, was synthesized in a 15 % overall yield, in ten steps, starting from the commercially available phloroacetophenone. The C-glucosyl phloroacetophenone derivative, a synthetic intermediate that contains a free hydroxyl group that is para to the glucosyl moiety, was obtained by hydrogenolysis by taking advantage of differences in the hydrogenolysis rates between a benzyl protecting group and a 2-methylbenzyl protecting group. Aldol condensation of the C-glucosyl phloroacetophenone derivative with 3,4-bis-benzyloxybenzaldehyde afforded the corresponding chalcone as a precursor of the 6-C-glucosyl flavone. Construction of the flavone system by application of I₂–DMSO, followed by deprotection, yielded isoorientin.