天然糖苷Cleistanthin-B的合成

Total Synthesis of Cleistanthin-B

天然萘基木脂素糖苷Cleistanthin-B具有升高白细胞的活性,为深入研究其药理作用机制,完成了Cleis-tanthin-B的化学全合成.采用Adol反应和Diels-Alder反应合成了萘基木脂素山荷叶素,然后以溴代乙酰葡萄糖为供体,四丁基溴化铵为催化剂,采用相转移催化法进行了山荷叶素的糖苷化反应,弱碱条件脱除乙酰基,以7步反应30.3%的总产率得到了Cleistanthin-B,并采用核磁共振氢谱、碳谱和高分辨质谱对目标化合物的结构进行了表征,谱图数据与天然产物的一致.

The naturally occurring diphyllin glucosidc cleistanthin-B can increase the activity of leucocyte. It was synthesized to investigate the mechanism of its pharmacological action. First, Diphyllin was prepared under Adol reaction and Diels-Aider reaction. Then, Cleistanthin-B was synthesized by the glycosyiation of diphyllin with peracetylglucosyl bromides under phase transfer catalysis conditions in seven steps at gross production rate of 30.3%. The structure of the composite was identified by 1H NMR, 13C NMR and HRMS, whose spectrum data were consistent with that of the natural Cleistanthin-B.