Articles producció científicaQuímica Analítica i Química Orgànica

Total Synthesis of Repraesentin F and Configuration Reassignment by a Gold(I)-Catalyzed Cyclization Cascade

  • Identification data

    Identifier:  imarina:9440779
    Handle: https://hdl.handle.net/20.500.11797/imarina9440779
    Authors:  Ferrer, Sofia; Echavarren, Antonio M
    Abstract:
    The first total synthesis of repraesentin F has been accomplished by a highly diastereoselective gold(I)-catalyzed cyclization cascade as the key step. This cycloisomerization/Prins-type tandem transformation enabled direct access to the atypical tricyclic carbon skeleton of the natural product with the required syn/anti/syn ring fusion. This synthetic effort also allowed reassignment of the relative configuration of repraesentin F and determination of its absolute configuration.

  • Others:

    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.8b02478
    APA: Ferrer, Sofia; Echavarren, Antonio M (2018). Total Synthesis of Repraesentin F and Configuration Reassignment by a Gold(I)-Catalyzed Cyclization Cascade. Organic Letters, 20(18), 5784-5788. DOI: 10.1021/acs.orglett.8b02478
    Paper original source: Organic Letters. 20 (18): 5784-5788
    Article's DOI: 10.1021/acs.orglett.8b02478
    Journal publication year: 2018
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    Record's date: 2025-02-18
    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
    Author, as appears in the article.: Ferrer, Sofia; Echavarren, Antonio M
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Química, Physical and theoretical chemistry, Organic chemistry, Medicina ii, Medicina i, Materiais, Interdisciplinar, General medicine, Farmacia, Ciências biológicas ii, Ciências biológicas i, Ciências agrárias i, Chemistry, organic, Biotecnología, Biodiversidade, Biochemistry
    Author's mail: antoniomaria.echavarren@urv.cat

  • Keywords:

    Sulcatine-g
    Structure elucidation
    Secondary mold metabolites
    Rearrangemen
    Protoilludane sesquiterpenes
    Plant-growth promoters
    Natural-products
    Lactarius-repraesentaneus
    Kelsoene
    Absolute-configuration
    Biochemistry
    Chemistry
    Organic
    Organic Chemistry
    Physical and Theoretical Chemistry
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Biotecnología
    Biodiversidade

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