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Total syntheses of pyrroloazocine indole alkaloids: challenges and reaction discovery
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2017-10-24 00:00:00 , DOI: 10.1039/c7qo00786h
Mariia S. Kirillova 1, 2, 3, 4 , Fedor M. Miloserdov 1, 2, 3, 4 , Antonio M. Echavarren 1, 2, 3, 4, 5
Affiliation  

Lapidilectines, grandilodines, lundurines and tenuisines are indole alkaloids, isolated from plants of Kopsia genus. They feature a common indole-fused pyrroloazocine core, whose construction poses a significant synthetic challenge. In this review, we discuss the reported strategies for the total synthesis of this family of alkaloids with a focus on the different methods used for the construction of spiro[cyclohexane-2-indoline] and indole-pyrroloazocine intermediates, introduction of indole-fused cyclopropane as well as other new methodologies uncovered in the course of the total syntheses. In closing, the existing hypothesis of the biosynthetic origin and relationships of the pyrroloazocine indole alkaloids are presented.

中文翻译:

吡咯并偶氮吲哚生物碱的总合成:挑战和反应发现

Lapidilectines,grandilodines,lundurines和tenuisines是从Kopsia属植物中分离出来的吲哚生物碱。它们具有常见的与吲哚融合的吡咯并恶唑啉核,其结构构​​成了重大的合成挑战。在这篇综述中,我们讨论了该生物碱家族的全合成报告的策略,重点是用于构建螺[环己烷-2-二氢吲哚]和吲哚-吡咯并恶唑啉中间体的不同方法,引入了吲哚-稠合的环丙烷以及在整个综合过程中发现的其他新方法。最后,介绍了生物合成起源的现有假设以及吡咯并偶氮吲哚生物碱的关系。
更新日期:2017-10-24
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