Jiangsu Key Laboratory for Functional Substance of Chinese Medicine, School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210023, China.
Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, Lexington, Kentucky 40536, United States.
J Am Chem Soc. 2020 May 20;142(20):9389-9395. doi: 10.1021/jacs.9b13766. Epub 2020 May 7.
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.
描述了一种利用天然产物壮观霉素来获得具有独特功能化的单糖的高效发散合成策略。关键壮观霉素衍生中间体的立体选择性 2'-和 3'-还原使得易于获得所有八种可能的 4,6-去氧己糖的 2,3-立体异构体以及代表性的 3,4,6-三脱氧糖和 3,4,6-三脱氧-3-氨基己糖。此外，该方法还应用于两种常见的与大环内酯抗生素相关的功能化糖的合成——3-烷基-4,6-去氧己糖 d-海藻糖和 3-烷基-3,4,6-三脱氧糖 d-去甲糖胺。
