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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, J; Livendahl, M; McGonigal, PR; Echavarren, AM
    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, J; Livendahl, M; McGonigal, PR; Echavarren, AM (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: 2014-05-05
    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
    Author, as appears in the article.: Carreras, J; Livendahl, M; McGonigal, PR; Echavarren, AM
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    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
    Total synthesi
    Terpenoids
    Sesquiterpenoids
    Rearrangement reactions
    Natural products
    Gold
    Essential oils
    Diterpenoids
    Cyclization
    Chemistr
    Catalyzed cycloisomerization
    Aromadendrane derivatives
    (+)-aromadendrene
    Catalysis
    Chemistry
    Chemistry (Miscellaneous)
    Multidisciplinary
    General medicine
    General chemistry
    Chemistry (all)
    Astronomia / física

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