An efficient first total synthesis of highly polar ulmoside A and (2R,3R)-taxifolin-6-C-β- d -glucopyranoside, useful for the prevention of metabolic disorders, has been described. Key elements of the synthesis include a Sc(OTf)3-catalyzed regio- and stereoselective C-glycosidation on taxifolin in 35% yield with d -glucose and chiral semipreparative reverse-phase high-performance liquid chromatography (HPLC) for the separation of both taxifolins and the diastereomeric mixture of taxifolin-6-C-β- d -glucopyranosides. Correlation of the analytical data of synthetic ulmoside A and its diastereomer with a natural ulmoside A sample confirmed the assigned absolute stereochemistry of the natural products.

中文翻译：

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天然产物乌莫苷 A 和 (2R,3R)-Taxifolin-6-C-β-d-吡喃葡萄糖苷的全合成

高极性ulmoside A 和(2R,3R)-taxifolin-6-C-β-d-吡喃葡萄糖苷的有效首次全合成已被描述，可用于预防代谢紊乱。合成的关键要素包括 Sc(OTf)3 催化的紫杉叶素上的区域选择性和立体选择性 C-糖苷化，产率为 35%，使用 d-葡萄糖和手性半制备反相高效液相色谱 (HPLC) 分离两者紫杉叶素和紫杉叶素-6-C-β-d-吡喃葡萄糖苷的非对映异构体混合物。合成 ulmoside A 及其非对映异构体与天然 ulmoside A 样品的分析数据的相关性证实了天然产物的指定绝对立体化学。