Open AccessChemical Access to d -Sarmentose Units Enables the Total Synthesis of Cardenolide Monoglycoside N-1 from Nerium oleander
Author(s) -
Jordi Mestre,
M. Isabel Matheu,
Yolanda Dı́az,
Sergio Castillón,
Omar Boutureira
Publication year - 2017
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.7b00210
Subject(s) - cardenolide , chemistry , stereoselectivity , wittig reaction , glycosylation , stereochemistry , total synthesis , chemical synthesis , trisaccharide , protecting group , glycoside , biochemistry , organic chemistry , in vitro , catalysis , alkyl
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.