天然黄酮碳糖苷化合物特有的稳定性和显著的生物活性,使其化学合成成为当今糖化学领域的研究热点之-.本工作立体专一性地全合成了天然黄酮碳苷Parkinsonin B.通过控制物质的量比,首先高选择性合成了2-羟基-4,6-二甲氧基苯乙酮(3),并与糖给体O-(2,3,4,6-四-O-苄基-α—D-葡萄糖基)三氯乙酰亚胺酯(7)发生立体专一性糖基化反应得到碳糖苷化合物8,化合物8经查耳酮路线进而合成黄酮碳苷Parkinsonin B(1).经IR,MS,^1H NMR及元素分析证实了产物及中间体的结构,同时讨论了全合成反应的主要影响因素,并对其^1H NMR解析进行了探讨.
Owing to their special stability and prominent biological activity, C-glycosylflavones and their chemical synthesis have recently attracted considerable attention in the field of glycoscience. A total synthesis of glycosylflavone parkinsonin B with specific stereoselectivity is reported herein. 2-Hydroxy-4,6-bismethoxy acetophenone (3) was synthesized by one step in high regioselectivity under the optimal condition. The compound 3 was then glycosylated with O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) trichloroacetimidate (7) as active glycosyl donor with specific stereoselectivity to produce compound 8. Parkinsonin B (1) was synthesized by the chalcone route from compound 8. The structures of target compound 1 and intermediates were confirmed by IR, MS, ^1H NMR spectra and element analysis.