TY - JOUR
T1 - Sugar-Pirating as an Enabling Platform for the Synthesis of 4,6-Dideoxyhexoses
AU - Zhang, Yinan
AU - Zhang, Jianjun
AU - Ponomareva, Larissa V.
AU - Cui, Zheng
AU - Van Lanen, Steven G.
AU - Thorson, Jon S.
AU - Thorson, Jon S.
N1 - Publisher Copyright:
© 2020 American Chemical Society.
PY - 2020/5/20
Y1 - 2020/5/20
N2 - An efficient divergent synthetic strategy that leverages the natural product spectinomycin to access uniquely functionalized monosaccharides is described. Stereoselective 2′- and 3′-reduction of key spectinomycin-derived intermediates enabled facile access to all eight possible 2,3-stereoisomers of 4,6-dideoxyhexoses as well as representative 3,4,6-trideoxysugars and 3,4,6-trideoxy-3-aminohexoses. In addition, the method was applied to the synthesis of two functionalized sugars commonly associated with macrolide antibiotics - the 3-O-alkyl-4,6-dideoxysugar d-chalcose and the 3-N-alkyl-3,4,6-trideoxysugar d-desosamine.
AB - An efficient divergent synthetic strategy that leverages the natural product spectinomycin to access uniquely functionalized monosaccharides is described. Stereoselective 2′- and 3′-reduction of key spectinomycin-derived intermediates enabled facile access to all eight possible 2,3-stereoisomers of 4,6-dideoxyhexoses as well as representative 3,4,6-trideoxysugars and 3,4,6-trideoxy-3-aminohexoses. In addition, the method was applied to the synthesis of two functionalized sugars commonly associated with macrolide antibiotics - the 3-O-alkyl-4,6-dideoxysugar d-chalcose and the 3-N-alkyl-3,4,6-trideoxysugar d-desosamine.
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U2 - 10.1021/jacs.9b13766
DO - 10.1021/jacs.9b13766
M3 - Article
C2 - 32330028
AN - SCOPUS:85086515859
SN - 0002-7863
VL - 142
SP - 9389
EP - 9395
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 20
ER -