摘要/Abstract

报道了L-鼠李烯糖与炔丙酯在Au（I）催化下通过分子间串联的1，3-酰氧基迁移/Ferrier重排策略，合成了C-乙烯基鼠李糖苷衍生物.通过同位素O¹⁸标记实验验证了C-糖基化机理.产物的绝对构型经X射线单晶衍射分析确定.利用噻唑蓝（MTT）法研究了产物的细胞毒活性，结果显示产物3i对人体胃癌细胞HGC-27具有良好的抑制作用，IC₅₀值为18.29 μmol·L^-1.该方法具有操作简单、高非对映选择性、反应条件温和等优点.
关键词: Ferrier重排, 鼠李糖苷, 细胞毒活性, 非对映选择
A novel gold(I)-catalyzed glycosylation method was described to synthesize C-vinyl-rhamnopyranoside derivatives using stable propargylic carboxylates and 3,4-di-O-acetyl-L-rhamnal as starting materials, based on the tandem intermolecular 1,3-acyloxy migration/Ferrier rearrangement. The C-glycosylation process has been verified by O¹⁸ isotopic labeling experiment, and the absolute configuration of synthesized products was determined by X-ray single crystal diffraction. The cytotoxic activity was investigated by methyl thiazolyl tetrazolium (MTT). It indicates that product 3i has strong inhibitory effect on human gastric cancer cells HGC-27 with IC₅₀ 18.29 μmol·L^-1. The described synthetic method was outstanding with easy-to-operate, high diastereoselectivity, and mild reaction condition.
Key words: Ferrier rearrangement, rhamnopyranoside, cytotoxic activity, diastereoselectivity


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