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: 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: sergio.castillon@urv.cat maribel.matheu@urv.cat yolanda.diaz@urv.cat

Author identifier: 0000-0002-0690-7549 0000-0001-5216-9260 0000-0001-5567-8108

Record's date: 2023-02-18

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: http://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