Articles producció científica> Química Analítica i Química Orgànica

Chemical Access to d -Sarmentose Units Enables the Total Synthesis of Cardenolide Monoglycoside N-1 from Nerium oleander

  • Identification data

    Identifier: PC:2710
    Authors:
    Matheu, M.I.Mestre, J.Díaz, Y.Castillón, S.Boutureira, O.
    Abstract:
    DOI: 10.1021/acs.joc.7b00210 URL: http://www.sciencedirect.com/science/article/pii/S0926337317301832 Filiació URV: SI
  • Others:

    Author, as appears in the article.: Matheu, M.I.; Mestre, J.; Díaz, Y.; Castillón, S. ; Boutureira, O.
    Department: Química Analítica i Química Orgànica
    URV's Author/s: MATHEU MALPARTIDA, MARÍA ISABEL; Mestre, J.; DÍAZ GIMÉNEZ, MARÍA YOLANDA; CASTILLÓN MIRANDA, SERGIO; Boutureira, O.
    Keywords: organic compounds Chemical synthesis
    Abstract: Herein we present a chemical approach for the ready preparation of d-sarmentosyl donors enabling the first total synthesis and structure validation of cardenolide N-1, a challenging 2,6-dideoxy-3-O-methyl-¿-d-xylo-hexopyranoside extracted from Nerium oleander twigs that displays anti-inflammatory properties and cell growth inhibitory activity against tumor cells. The strategy highlights the synthetic value of the sequential methodology developed in our group for the synthesis of 2-deoxyglycosides. Key steps include Wittig-Horner olefination of a d-xylofuranose precursor, [I+]-induced 6-endo cyclization, and 1,2-trans stereoselective glycosylation.
    Research group: Síntesis Orgànica Estereoselectiva
    Thematic Areas: Química Química Chemistry
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 0022-3263
    Author identifier: ; n/a; ; ; 0000-0002-0768-8309
    Record's date: 2017-04-04
    Last page: 3333
    Journal volume: 82
    Papper version: info:eu-repo/semantics/publishedVersion
    Link to the original source: http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b00210
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Article's DOI: 10.1021/acs.joc.7b00210
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2017
    First page: 3327
    Publication Type: Article Artículo Article
  • Keywords:

    Compostos orgànics -- Síntesi
    Tumors -- Tractament
    organic compounds
    Chemical synthesis
    Química
    Química
    Chemistry
    0022-3263
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