天然产物Chimonanthine的全合成研究进展

Progress in total synthesis of chimonanthine

在吲哚生物碱大家族中,其中有一类化合物是以色氨的二聚、三聚甚至多聚的形式存在于自然界中,它们就是吸引有机化学家们广泛研究兴趣的环色胺类生物碱。Chimonanthine则是这个大家族中最简单最重要的一类化合物。根据其旋光性的不同,Chimonanthine有meso-Chimonanthine、(+)-Chimonanthine和(-)-Chimonanthine 3种类型。由于Chimonanthine在环色胺类吲哚生物碱中有着特殊的地位,所以早在20世纪60年代Woodward等就推测,该化合物在生物体内的合成主要是通过自由基偶联发生两分子的聚合。从推测Chimonanthine的生物合成途径开始,综述了近些年来Chimo-nanthine的全合成研究进展,并对各类合成途径的反应条件、反应选择性、产率以及机理的研究进行了讨论和总结。

The dimmers, trimers, and higher-order oligomers of tryptamine are the most abundant indoline alkaloids in na- ture. These compounds that fascinating family of natural prod- ucts is complex cyclotryptamine alkaloids. In which one is chimonanthine,although a simple structure, occupies an im- portant position. According to the optical activity, chimonan- thine includes three compounds： meso-chimonanthine, （ ＋ ）- chimonanthine and （ - ）-chimonanthine. Due to the impor- tance of chimonanthine,in the early of 1960 s, Woodward and coworkers supposed that there is a radical coupling reaction in the living organism. Beginning with a suppose of biological pathways,recent development of the total synthesis of chimo- nanthine is reviewed, reaction conditions, selectivity, yields and mechanisms are discussed and summarized.