Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers |
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| Authors: | Dr. Shengyang Wang Prof. Jiansong Sun Qingju Zhang Dr. Xin Cao Yachen Zhao Prof. Gongli Tang Prof. Biao Yu |
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| Affiliation: | 1. http://biaoyu.sioc.ac.cn;2. 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, Shanghai, China;3. The National Engineering Research Centre for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang, China |
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| Abstract: | 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. |
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| Keywords: | amino acids antibiotics glycosylation gold natural products |
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