Articles producció científica> Química Analítica i Química Orgànica

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

  • Dades identificatives

    Identificador: imarina:9440779
    Autors:
    Ferrer, SofiaEchavarren, Antonio M
    Resum:
    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.
  • Altres:

    Autor segons l'article: Ferrer, Sofia; Echavarren, Antonio M
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: ECHAVARREN PABLOS, ANTONIO
    Paraules clau: Sulcatine-g Structure elucidation Secondary mold metabolites Rearrangemen Protoilludane sesquiterpenes Plant-growth promoters Natural-products Lactarius-repraesentaneus Kelsoene Absolute-configuration
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: antoniomaria.echavarren@urv.cat
    Identificador de l'autor: 0000-0002-6418-7930
    Data d'alta del registre: 2025-02-18
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Referència a l'article segons font original: Organic Letters. 20 (18): 5784-5788
    Referència de l'ítem segons les normes 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
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Tipus de publicació: Journal Publications
  • Paraules clau:

    Biochemistry,Chemistry, Organic,Organic Chemistry,Physical and Theoretical Chemistry
    Sulcatine-g
    Structure elucidation
    Secondary mold metabolites
    Rearrangemen
    Protoilludane sesquiterpenes
    Plant-growth promoters
    Natural-products
    Lactarius-repraesentaneus
    Kelsoene
    Absolute-configuration
    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
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