Articles producció científicaQuímica Analítica i Química Orgànica

Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step

  • Identification data

    Identifier:  imarina:6069429
    Handle: https://hdl.handle.net/20.500.11797/imarina6069429
    Authors:  Scharnagel, D; Escofet, I; Armengol-Relats, H; de Orbe, ME; Korber, JN; Echavarren, AM
    Abstract:
    The gold(I)-catalyzed reaction of acetylene gas with alkenes leads to (Z,Z)-1,4-disubstituted 1,3-butadienes and biscyclopropanes depending on the donor ligand on gold(I). Acetylene was generated in situ from calcium carbide and water in a user-friendly procedure. Reaction of acetylene with 1,5-dienes gives rise stereoselectively to tricyclo[5.1.0.0(2,4)]octanes. This novel double cyclopropanation has been applied to the one step total synthesis of the natural product waitziacuminone from acetylene and geranyl acetone.

  • Others:

    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201915895
    APA: Scharnagel, D; Escofet, I; Armengol-Relats, H; de Orbe, ME; Korber, JN; Echavarren, AM (2020). Acetylene as a Dicarbene Equivalent for Gold(I) Catalysis: Total Synthesis of Waitziacuminone in One Step. Angewandte Chemie (International Ed. Print), 59(12), 4888-4891. DOI: 10.1002/anie.201915895
    Paper original source: Angewandte Chemie (International Ed. Print). 59 (12): 4888-4891
    Article's DOI: 10.1002/anie.201915895
    Journal publication year: 2020-03-16
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2026-05-09
    URV's Author/s: ECHAVARREN PABLOS, ANTONIO
    Department: Química Analítica i Química Orgànica
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Publication Type: Journal Publications
    ISSN: 1433-7851
    Author, as appears in the article.: Scharnagel, D; Escofet, I; Armengol-Relats, H; de Orbe, ME; Korber, JN; Echavarren, AM
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Journal volume: 59
    Thematic Areas: General medicine, General chemistry, Chemistry, multidisciplinary, Chemistry (miscellaneous), Chemistry (all), Chemistry, Catalysis, Astronomia / física
    Author's mail: antoniomaria.echavarren@urv.cat, antoniomaria.echavarren@urv.cat

  • Keywords:

    Total synthesis
    Intermolecular 2+2 cycloaddition
    Gold catalysis
    Cyclopropanation
    Constituents
    Alkynes
    Alkenes
    Acetylene
    Catalysis
    Chemistry
    Chemistry (Miscellaneous)
    Multidisciplinary
    General medicine
    General chemistry
    Chemistry (all)
    Astronomia / física

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