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, S; Echavarren, AM
    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, S; Echavarren, AM (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: 2018-09-21
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/acceptedVersion
    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
    Author, as appears in the article.: Ferrer, S; Echavarren, AM
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Physical and theoretical chemistry, Organic chemistry, General medicine, Chemistry, organic, Biotecnología, Biodiversidade, Biochemistry
    Author's mail: antoniomaria.echavarren@urv.cat, 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
    General medicine
    Biotecnología
    Biodiversidade

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