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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。
Among the large family of indole alkaloids, one of these compounds is found in nature in the dimeric, trimeric and even poly-polymeric forms of tryptophane, which are cycloamine amine alkaloids that attract organic chemists’ extensive research interest . Chimonanthine is the simplest and most important class of compounds in this large family. Chimonanthine has three types of meso-Chimonanthine, (+) - Chimonanthine and (-) - Chimonanthine, depending on their optical activity. Since Chimonanthine has a special place in the tryptamine class of indole alkaloids, Woodward et al. Hypothesized that the biosynthesis of this compound occurs predominantly by the two-molecule polymerization via free radical coupling as early as the 1960s. Starting from the biosynthetic pathway of Chimonanthine, the progress of total synthesis of Chimo-nanthine in recent years is reviewed. The reaction conditions, reaction selectivity, yield and mechanism of Chimoanthine are also discussed and summarized.