Total Synthesis of Lundurine and Related Alkaloids: Synthetic Approaches and Strategies
Total Synthesis of Lundurine and Related Alkaloids: Synthetic Approaches and Strategies
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DOI：
10.1016/bs.alkal.2017.01.001
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发表时间：
2017-01-01
影响因子：
--
通讯作者：
Nishida, Atsushi
中科院分区：
文献类型：
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作者：
Arai, Shigeru;Nakajima, Masaya;Nishida, Atsushi
本综述重点关注 Lundurines A-C 的全合成。它们的主要结构特征是仅在这些生物碱中发现的独特的环丙[b]吲哚核心。除了这种特征结构之外，生物活性也使它们成为有吸引力的合成靶标。然而，从 1995 年分离和结构确定到首次全合成，已经过去了近二十年。本综述的第一部分总结了 Lundurine 三环和四环系统的合成方法，以及产生环丙[b]吲哚核心的分子间和分子内环丙烷化策略。第二部分详细描述了2014年至2016年报道的四个全合成。此外，还描述了相关生物碱grandilodine C和lapidilectine B的不对称全合成。
This review focuses on the total synthesis of lundurines A-C. Their main structural feature is a unique cyclopropa[b]indole core that has been found only in these alkaloids. In addition to this characteristic structure, the biological activity makes them as attractive synthetic targets. However, almost two decades passed from their isolation and structural determination in 1995 to their first total synthesis. The first part of this review summarizes the synthetic approaches to the tri- and tetracyclic ring systems of lundurine as well as an inter-and intramolecular cyclopropanation strategy that gives the cyclopropa[b]indole core. The second part presents a detailed description of four total syntheses that were reported from 2014 to 2016. In addition, the asymmetric total synthesis of the related alkaloids grandilodine C and lapidilectine B is described.