title: Chemical Access to d-Sarmentose Units Enables the Total Synthesis of Cardenolide Monoglycoside N-1 from Nerium oleander.
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-β-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.
authors.affiliation: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili , C/Marcel·lí Domingo 1, 43007 Tarragona, Spain.
authors.forename: Jordi
authors.identifier: 0000-0002-4279-350X
authors.initials: J
authors.lastname: Mestre
authors.affiliation: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili , C/Marcel·lí Domingo 1, 43007 Tarragona, Spain.
authors.forename: M Isabel
authors.initials: MI
authors.lastname: Matheu
authors.affiliation: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili , C/Marcel·lí Domingo 1, 43007 Tarragona, Spain.
authors.forename: Yolanda
authors.initials: Y
authors.lastname: Díaz
authors.affiliation: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili , C/Marcel·lí Domingo 1, 43007 Tarragona, Spain.
authors.forename: Sergio
authors.initials: S
authors.lastname: Castillón
authors.affiliation: Departament de Química Analítica i Química Orgànica, Universitat Rovira i Virgili , C/Marcel·lí Domingo 1, 43007 Tarragona, Spain.
authors.forename: Omar
authors.identifier: 0000-0002-0768-8309
authors.initials: O
authors.lastname: Boutureira