Open AccessSugar-Pirating as an Enabling Platform for the Synthesis of 4,6-Dideoxyhexoses
Author(s) -
Yinan Zhang,
Jianjun Zhang,
Larissa V. Ponomareva,
Zheng Cui,
Steven G. Van Lanen,
Jon S. Thorson
Publication year - 2020
Publication title -
journal of the american chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 7.115
H-Index - 612
eISSN - 1520-5126
pISSN - 0002-7863
DOI - 10.1021/jacs.9b13766
Subject(s) - chemistry , stereoselectivity , spectinomycin , monosaccharide , natural product , sugar , alkyl , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , antibiotics , catalysis , antibiotic resistance
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.