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Concise Total Synthesis of Lundurines A-C Enabled by Gold Catalysis and a Homodienyl Retro-Ene/Ene Isomerization

  • Datos identificativos

    Identificador: PC:1532
    Autores:
    Antonio M. EchavarrenMariia S. KirillovaMichael E. MuratoreRuth Dorel
    Resumen:
    The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.
  • Otros:

    Autor según el artículo: Antonio M. Echavarren; Mariia S. Kirillova; Michael E. Muratore; Ruth Dorel
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: ECHAVARREN PABLOS, ANTONIO MARIA; Mariia S. Kirillova; Michael E. Muratore; Ruth Dorel
    Palabras clave: Synthesis (chemical) Gold catalysis
    Resumen: The total synthesis of lundurines A-C has been accomplished in racemic and enantiopure forms in 11-13 and 12-14 steps, respectively, without protection/deprotection of functional groups, by a novel tandem double condensation/Claisen rearrangement, a gold(I)-catalyzed alkyne hydroarylation, a cyclopropanation via formal [3 + 2] cycloaddition/nitrogen extrusion, and a remarkable olefin migration through a vinylcyclopropane retro-ene/ene reaction that streamlines the endgame.
    Áreas temáticas: Química Química Chemistry
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0002-7863
    Identificador del autor: 0000-0001-6808-3007; n/a; n/a; n/a
    Fecha de alta del registro: 2016-05-02
    Página final: 3674
    Volumen de revista: 138
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2016
    Página inicial: 3671
    Tipo de publicación: Article Artículo Article
  • Palabras clave:

    Catàlisi
    Or
    Synthesis (chemical)
    Gold catalysis
    Química
    Química
    Chemistry
    0002-7863
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