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: imarina:5130916
    Handle: https://hdl.handle.net/20.500.11797/imarina5130916
    Authors:
    Mestre J, Matheu MI, 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, 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.

  • Others:

    Author, as appears in the article.: Mestre J, Matheu MI, Díaz Y, Castillón S, Boutureira O
    Department: Química Analítica i Química Orgànica
    URV's Author/s: Boutureira Martín, Omar / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
    Keywords: Stereoselective glycosylation Organic compounds D-sarmentosyl donors 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.
    Thematic Areas: Química Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ensino Engenharias iv Engenharias ii Engenharias i Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Astronomia / física
    licence for use: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 00223263
    Author's mail: omar.boutureira@urv.cat yolanda.diaz@urv.cat maribel.matheu@urv.cat sergio.castillon@urv.cat
    Author identifier: 0000-0002-0768-8309 0000-0001-5567-8108 0000-0001-5216-9260 0000-0002-0690-7549
    Record's date: 2024-09-07
    Papper version: info:eu-repo/semantics/acceptedVersion
    Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
    Papper original source: Journal Of Organic Chemistry. 82 (6): 3327-3333
    APA: Mestre J, Matheu MI, Díaz Y, Castillón S, Boutureira O (2017). Chemical Access to d -Sarmentose Units Enables the Total Synthesis of Cardenolide Monoglycoside N-1 from Nerium oleander. Journal Of Organic Chemistry, 82(6), 3327-3333. DOI: 10.1021/acs.joc.7b00210
    Entity: Universitat Rovira i Virgili
    Journal publication year: 2017
    Publication Type: Journal Publications

  • Keywords:

    Chemistry, Organic,Organic Chemistry
    Stereoselective glycosylation
    Organic compounds
    D-sarmentosyl donors
    Chemical synthesis
    Química
    Organic chemistry
    Odontología
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ensino
    Engenharias iv
    Engenharias ii
    Engenharias i
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Ciência de alimentos
    Chemistry, organic
    Biotecnología
    Astronomia / física

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