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Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (-)-Epiglobulol and (-)-4β,7α- and (-)-4α,7α-Aromadendranediols

  • Identification data

    Identifier:  imarina:9440806
    Handle: https://hdl.handle.net/20.500.11797/imarina9440806
    Authors:  Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R; Echavarren, Antonio M
    Abstract:
    Three natural aromadendrane sesquiterpenes, (-)-epiglobulol, (-)-4,7-aromadendranediol, and (-)-4,7-aromadendranediol, have been synthesized in only seven steps in 12, 15, and 17% overall yields, respectively, from (E,E)-farnesol by a stereodivergent gold(I)-catalyzed cascade reaction which forms the tricyclic aromadendrane core in a single step. These are the shortest total syntheses of these natural compounds.

  • Others:

    Link to the original source: https://onlinelibrary.wiley.com/doi/full/10.1002/anie.201402044
    APA: Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R; Echavarren, Antonio M (2014). Gold(I) as an Artificial Cyclase: Short Stereodivergent Syntheses of (-)-Epiglobulol and (-)-4β,7α- and (-)-4α,7α-Aromadendranediols. Angewandte Chemie (International Ed. Print), 53(19), 4896-4899. DOI: 10.1002/anie.201402044
    Paper original source: Angewandte Chemie (International Ed. Print). 53 (19): 4896-4899
    Article's DOI: 10.1002/anie.201402044
    Journal publication year: 2014
    Entity: Universitat Rovira i Virgili
    Paper version: info:eu-repo/semantics/publishedVersion
    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.: Carreras, Javier; Livendahl, Madeleine; McGonigal, Paul R; Echavarren, Antonio M
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    Thematic Areas: Química, Medicina ii, Medicina i, Materiais, Interdisciplinar, General medicine, General chemistry, Farmacia, Engenharias ii, Ciências biológicas iii, Ciências biológicas ii, Ciências biológicas i, Chemistry, multidisciplinary, Chemistry (miscellaneous), Chemistry (all), Chemistry, Catalysis, Astronomia / física
    Author's mail: antoniomaria.echavarren@urv.cat

  • Keywords:

    Total synthesis
    Total synthesi
    Terpenoids
    Sesquiterpenoids
    Rearrangement reactions
    Natural products
    Gold
    Essential oils
    Diterpenoids
    Cyclization
    Chemistr
    Catalyzed cycloisomerization
    Aromadendrane derivatives
    (+)-aromadendrene
    Catalysis
    Chemistry
    Chemistry (Miscellaneous)
    Multidisciplinary
    Química
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    General chemistry
    Farmacia
    Engenharias ii
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Chemistry (all)
    Astronomia / física

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