Chemical Access to d‑Sarmentose Units Enables the Total Synthesis of Cardenolide Monoglycoside N‑1 from Nerium oleander

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 pr...

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Bibliographic Details
Published in:Journal of organic chemistry 2017-03, Vol.82 (6), p.3327-3333
Main Authors: Mestre, Jordi, Matheu, M. Isabel, Díaz, Yolanda, Castillón, Sergio, Boutureira, Omar
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00210