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Total syntheses of pyrroloazocine indole alkaloids: Challenges and reaction discovery

  • Datos identificativos

    Identificador: imarina:9380483
    Autores:
    Kirillova MSMiloserdov FMEchavarren AM
    Resumen:
    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.
  • Otros:

    Autor según el artículo: Kirillova MS; Miloserdov FM; Echavarren AM
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: ECHAVARREN PABLOS, ANTONIO
    Resumen: 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.
    Áreas temáticas: Chemistry, organic Organic chemistry
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: antoniomaria.echavarren@urv.cat
    Identificador del autor: 0000-0002-6418-7930
    Fecha de alta del registro: 2024-09-21
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Referencia al articulo segun fuente origial: Organic Chemistry Frontiers. 5 (2): 273-287
    Referencia 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 Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2018
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Chemistry, Organic,Organic Chemistry
    Chemistry, organic
    Organic chemistry
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