Articles producció científica> Química Analítica i Química Orgànica

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

  • Identification data

    Identifier: PC:1532
    Authors:
    Antonio M. EchavarrenMariia S. KirillovaMichael E. MuratoreRuth Dorel
    Abstract:
    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.
  • Others:

    Author, as appears in the article.: Antonio M. Echavarren; Mariia S. Kirillova; Michael E. Muratore; Ruth Dorel
    Department: Química Analítica i Química Orgànica
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO MARIA; Mariia S. Kirillova; Michael E. Muratore; Ruth Dorel
    Keywords: Synthesis (chemical) Gold catalysis
    Abstract: 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.
    Thematic Areas: Química Química Chemistry
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0002-7863
    Author identifier: 0000-0001-6808-3007; n/a; n/a; n/a
    Record's date: 2016-05-02
    Last page: 3674
    Journal volume: 138
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: https://pubs.acs.org/doi/10.1021/jacs.6b01428
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1021/jacs.6b01428
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2016
    First page: 3671
    Publication Type: Article Artículo Article
  • Keywords:

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