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:3122
    Authors:
    Matheu, M. I.Mestre, J.Díaz, Y.Castillón, S.Boutureira, O.
    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, 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
  • 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: d-sarmentosyl donors stereoselective glycosylation
    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, 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: 0000-0001-5216-9260; ; 0000-0001-5567-8108; 0000-0002-0690-7549;
    Record's date: 2018-02-28
    Last page: 3333
    Journal volume: 82
    Papper version: info:eu-repo/semantics/acceptedVersion
    Link to the original source: https://pubs.acs.org/doi/abs/10.1021/acs.joc.7b00210
    Funding program: plan; Excelencia; CTQ2014-58664-R plan; RYC-2015-17705
    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:

    Glicosilació
    Estereoquímica
    d-sarmentosyl donors
    stereoselective glycosylation
    Química
    Química
    Chemistry
    0022-3263
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