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

  • Dades identificatives

    Identificador: imarina:5130916
    Autors:
    Mestre J, Matheu MI, Díaz Y, Castillón S, Boutureira O
    Resum:
    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.
  • Altres:

    Autor segons l'article: Mestre J, Matheu MI, Díaz Y, Castillón S, Boutureira O
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Boutureira Martín, Omar / Castillón Miranda, Sergio / Díaz Giménez, María Yolanda / Matheu Malpartida, María Isabel
    Paraules clau: Stereoselective glycosylation Organic compounds D-sarmentosyl donors Chemical synthesis
    Resum: 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    ISSN: 00223263
    Adreça de correu electrònic de l'autor: omar.boutureira@urv.cat yolanda.diaz@urv.cat maribel.matheu@urv.cat sergio.castillon@urv.cat
    Identificador de l'autor: 0000-0002-0768-8309 0000-0001-5567-8108 0000-0001-5216-9260 0000-0002-0690-7549
    Data d'alta del registre: 2024-09-07
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.acs.org/doi/10.1021/acs.joc.7b00210
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Journal Of Organic Chemistry. 82 (6): 3327-3333
    Referència de l'ítem segons les normes 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
    DOI de l'article: 10.1021/acs.joc.7b00210
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2017
    Tipus de publicació: Journal Publications
  • Paraules clau:

    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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