Total synthesis of kopsine, fruticosine, and structurally related polycyclic caged Kopsia indole alkaloids

Total synthesis of kopsine, fruticosine, and structurally related polycyclic caged Kopsia indole alkaloids
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Kopsine、frutecosine 和结构相关的多环笼状 Kopsia 吲哚生物碱的全合成

DOI:
10.1039/d0qo01165g
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发表时间:
2020-11
影响因子:
5.4
通讯作者:
Jia Yanxing
Jia Yanxing
中科院分区:
化学1区
文献类型:
--
作者:
Qin Bo;Wang Yuan;Wang Xin;Jia Yanxing

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自1983年以来,Kopsine,fruticosine和相关的笼状和多环Kopsia吲哚生物碱一直是有吸引力的合成目标。除了具有良好的生物活性外,多个连续的立体发生中心(包括嵌入刚性和笼状多环骨架中的两个全碳四元立体中心)在合成化学中提出了重大挑战。由于这些合成目标的结构极其复杂,人们付出了巨大的努力。本文综述了近年来国内外对Kopsine、fruticosine及相关Kopsia吲哚生物碱的全合成研究进展,重点介绍了多环骨架的构建策略和C7/C20立体中心的构建方法。
Kopsine, fruticosine and related caged and polycyclic Kopsia indole alkaloids have been attractive synthetic targets since 1983. Besides their promising bioactivities, the multiple continuous stereogenetic centers including two all-carbon quaternary stereocenters embedded in a rigid and caged polycyclic skeleton poses significant challenges in synthetic chemistry. Due to the extrodinary complex structures, tremendous efforts have been devoted to these synthetic targets. In this review, we discuss reported strategies for the total synthesis of kopsine, fruticosine and related Kopsia indole alkaloids with an emphasis on tactics to construct the polycyclic skeleton and methodologies to install the C7/C20 stereocenters.
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