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

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