Mesh : Hydrolyzable Tannins / chemistry pharmacology chemical synthesis Molecular Structure Glycosides / chemistry chemical synthesis pharmacology Glycoside Hydrolases / antagonists & inhibitors Enzyme Inhibitors / chemical synthesis pharmacology chemistry Catalysis

来  源:   DOI:10.1021/acs.joc.4c00755

Abstract:
We report the first total synthesis of scleropentaside D, a unique C-glycosidic ellagitannin, from the ketal derivative of scleropentaside A employing site-selective O4-protection of C-acyl glycoside and copper-catalyzed oxidative coupling reaction of galloyl groups as the key steps. Our study confirms the proposed structure of this natural product, scleropentaside D, and demonstrates its effectiveness as an inhibitor of α-glycosidase.
摘要:
我们报道了硬化剂D的第一次全合成,一种独特的C-糖苷鞣质,来自scleropentasideA的缩酮衍生物,采用C-酰基糖苷的位点选择性O4保护和铜催化的没食子酰的氧化偶联反应作为关键步骤。我们的研究证实了这种天然产物的拟议结构,scleropentasideD,并证明了其作为α-糖苷酶抑制剂的有效性。
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