氨苯砜：结构和非对映异构体的全合成建议。
Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers.
机构信息
State Key Laboratory of Bioorganic and Natural Products Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
The National Engineering Research Centre for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, 330022, China.
出版信息
Angew Chem Int Ed Engl. 2018 Mar 5;57(11):2884-2888. doi: 10.1002/anie.201800169. Epub 2018 Feb 12.
The proposed diastereoisomers (1 a-d) together with their C8'-epimers (1 e-h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereocontrolled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C3' in amipurimycin should be of opposite configuration.
首次合成了独特的抗真菌肽核苷抗生素阿米普霉素的对映异构体（1a-d）及其 C8'-差向异构体（1e-h）。该合成方法高效且立体发散，具有立体选择性的醛缩合反应，构建支化的 C9 糖氨基酸骨架，以及区域和立体控制的金（I）催化的 N-糖苷化反应，生成嘌呤核苷。NMR 数据分析表明，阿米普霉素中先前被指定的 C3' 叔碳的构型应该具有相反的构型。
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