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
Link to the original source: https://pubs.acs.org/doi/10.1021/acs.joc.7b00210
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
Article's DOI: 10.1021/acs.joc.7b00210
Entity: Universitat Rovira i Virgili
Journal publication year: 2017
Publication Type: Journal Publications
Repositori URV