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Total syntheses of pyrroloazocine indole alkaloids: challenges and reaction discovery

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Abstract

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.

Graphical abstract: Total syntheses of pyrroloazocine indole alkaloids: challenges and reaction discovery

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Publication details

The article was received on 31 Aug 2017, accepted on 23 Oct 2017 and first published on 24 Oct 2017


Article type: Review Article
DOI: 10.1039/C7QO00786H
Citation: Org. Chem. Front., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    Total syntheses of pyrroloazocine indole alkaloids: challenges and reaction discovery

    M. S. Kirillova, F. M. Miloserdov and A. M. Echavarren, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO00786H

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