Articles producció científicaQuímica Analítica i Química Orgànica

Synthesis of Daucane Natural Products Enabled by a Gold(I)-Catalyzed Tandem Cycloisomerization/(4+3) Cycloaddition

  • Identification data

    Identifier:  imarina:9448902
    Handle: https://hdl.handle.net/20.500.11797/imarina9448902
    Authors:  Martí, A; Armengol-Relats, H; Sadurní, A; Pérez-Puigdomènech, MA; Echavarren, AM
    Abstract:
    A divergent synthesis of three members of the daucane family of natural products is reported, enabled by a gold(I)-catalyzed cycloisomerization/formal (4 + 3) cycloaddition as the key step. The synthesis of penigrisacid A features a vanadium-catalyzed tandem epoxidation/SN2 ' cyclization, whereas a Suarez radical cyclization enables the synthesis of aspterric acid. This work has also led to the reassignment of the structure of penigrisacid A as well as a short formal synthesis of schisanwilsonene A.

  • Others:

    Link to the original source: https://pubs.acs.org/doi/10.1021/acs.orglett.4c04542
    APA: Martí, A; Armengol-Relats, H; Sadurní, A; Pérez-Puigdomènech, MA; Echavarren, AM (2025). Synthesis of Daucane Natural Products Enabled by a Gold(I)-Catalyzed Tandem Cycloisomerization/(4+3) Cycloaddition. Organic Letters, 27(10), 2305-2309. DOI: 10.1021/acs.orglett.4c04542
    Paper original source: Organic Letters. 27 (10): 2305-2309
    Article's DOI: 10.1021/acs.orglett.4c04542
    Journal publication year: 2025-02-27
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    Record's date: 2026-02-13
    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.: Martí, A; Armengol-Relats, H; Sadurní, A; Pérez-Puigdomènech, MA; Echavarren, AM
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Biochemistry, Biodiversidade, Biotecnología, Chemistry, organic, Ciências agrárias i, Ciências biológicas i, Ciências biológicas ii, Farmacia, General medicine, Interdisciplinar, Materiais, Medicina i, Medicina ii, Organic chemistry, Physical and theoretical chemistry, Química
    Author's mail: antoniomaria.echavarren@urv.cat

  • Keywords:

    (+)-schisanwilsonene
    Abstractio
    Carotane
    Dl-aspterric acid
    Sesquiterpenoids
    Biochemistry
    Chemistry
    Organic
    Organic Chemistry
    Physical and Theoretical Chemistry
    Biodiversidade
    Biotecnología
    Ciências agrárias i
    Ciências biológicas i
    Ciências biológicas ii
    Farmacia
    General medicine
    Interdisciplinar
    Materiais
    Medicina i
    Medicina ii
    Química

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