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Synthesis of (3S,4R)-bengamide E
Authors:Qi Jun Liu  Hong Li a Guangzhou Institutes of Biomedicine  Health  Chinese Academy of Sciences  Guangzhou  China b Graduate School of Chinese Academy of Sciences  Beijing  China c College of Pharmaceutical Sciences  Nanjing University of Technology  Nanjing  China
Institution:a Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, Guangzhou 510530, China;b Graduate School of Chinese Academy of Sciences, Beijing 100039, China;c College of Pharmaceutical Sciences, Nanjing University of Technology, Nanjing 210009, China
Abstract:(3S,4R)-Bengamide E(2) was synthesized starting from D-glucono-δ-lactone(3) and the key deoxygenation step from 13 to 15 was achieved by the application of NaBH3CN and ZnI2.Compared with natural bengamide E(1),the synthetic compound(35,4R)-bengamide E(2) was inactive against the cell growth of HUVEC and cancer cells.These data represent the significance of the stereochemistry at C-3 and C-4 of bengamides for structural recognition and binding with the target(s).
Keywords:(3S  4R)-Bengamide E  Stereocenter  Deoxygenation  
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