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Total syntheses of pyrroloazocine indole alkaloids: Challenges and reaction discovery

  • Identification data

    Identifier: imarina:9380483
    Authors:
    Kirillova MSMiloserdov FMEchavarren AM
    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.
  • Others:

    Author, as appears in the article.: Kirillova MS; Miloserdov FM; Echavarren AM
    Department: Química Analítica i Química Orgànica
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO
    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.
    Thematic Areas: Chemistry, organic Organic chemistry
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Author's mail: antoniomaria.echavarren@urv.cat
    Author identifier: 0000-0002-6418-7930
    Record's date: 2024-09-21
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2018/qo/c7qo00786h
    Papper original source: Organic Chemistry Frontiers. 5 (2): 273-287
    APA: Kirillova MS; Miloserdov FM; Echavarren AM (2018). Total syntheses of pyrroloazocine indole alkaloids: Challenges and reaction discovery. Organic Chemistry Frontiers, 5(2), 273-287. DOI: 10.1039/c7qo00786h
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1039/c7qo00786h
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2018
    Publication Type: Journal Publications
  • Keywords:

    Chemistry, Organic,Organic Chemistry
    Chemistry, organic
    Organic chemistry
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