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--alkyl-4,6-dideoxysugar d-chalcose and the 3--alkyl-3,4,6-trideoxysugar d-desosamine.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7453097 | PMC |
| http://dx.doi.org/10.1021/jacs.9b13766 | DOI Listing |
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Sugar-Pirating as an Enabling Platform for the Synthesis of 4,6-Dideoxyhexoses.
J Am Chem Soc
May 2020
Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Lexington, Kentucky 40536, United States.
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--alkyl-4,6-dideoxysugar d-chalcose and the 3--alkyl-3,4,6-trideoxysugar d-desosamine.
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