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Total syntheses of pyrroloazocine indole alkaloids: Challenges and reaction discovery

  • Dades identificatives

    Identificador: imarina:9380483
    Autors:
    Kirillova MSMiloserdov FMEchavarren AM
    Resum:
    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.
  • Altres:

    Autor segons l'article: Kirillova MS; Miloserdov FM; Echavarren AM
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: ECHAVARREN PABLOS, ANTONIO
    Resum: 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.
    Àrees temàtiques: Chemistry, organic Organic chemistry
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: antoniomaria.echavarren@urv.cat
    Identificador de l'autor: 0000-0002-6418-7930
    Data d'alta del registre: 2024-09-21
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.rsc.org/en/content/articlelanding/2018/qo/c7qo00786h
    Referència a l'article segons font original: Organic Chemistry Frontiers. 5 (2): 273-287
    Referència de l'ítem segons les normes 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
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    DOI de l'article: 10.1039/c7qo00786h
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Chemistry, Organic,Organic Chemistry
    Chemistry, organic
    Organic chemistry
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