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制备4-羰基鬼臼毒的新方法及其产物的立体化学研究

A new method to prepare 4-carbonylpodophyllotoxin and stereochemistry of the product obtained
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摘要 目的 寻找制备 4-羰基鬼臼毒的新方法和高效试剂。方法 在室温条件下 ,溶解在丙酮中的鬼臼毒 (化合物 1 )被高锰酸钾的丙酮溶液稳定地氧化为标题化合物 ,反应体系中加入一定量的硫酸镁以中和反应产生的碱和吸收反应产生的水份 ,从而阻止鬼臼毒在碱性条件下的差向异构化和水解。结果 用质谱 (MS) ,核磁共振氢谱 (H1 NMR) ,研究了得到产物的分子结构和立体化学 ,证明它是 [1R - ( 1α,2α ,3β) ]- 4-羰基鬼臼毒素。结论 没有发现开环的副反应和手性碳原子的差向异构化 ,用高锰酸钾的丙酮溶液氧化制备标题化合物 ,是一种理想的制备 Objective To look for a new method of preparation for 4-carbonyl-podophyllotoxin and a new agent to oxidize podophyllotoxin.Methods In the room temperature ,podophyllotoxin dissolved in acetone was oxidized by the solution of potassium permanganate in acetone smoothly, and some of magnesium sulfate was added to the reaction mixture when the reaction begin to neutralize alkalescence produced by the reaction as well as to absorb water produced.Results The structure and absolute configuration of the product obtained was studied by MS, H 1nmr. It was proved that construction and configuration of the compound obtained is [1R-(1α,2α,3β)]-4-carbonyl-podophyllotoxin.Conclusion No side reactions including epimerization as well as other reaction in which the rings of podophyllotoxin would be broken were discovered. Therefore, the system of oxidants obtained is satisfactory.
出处 《兰州医学院学报》 2002年第4期11-13,共3页 Journal of Lanzhou Medical College
基金 甘肃省教育厅资助项目 (988- 12 )
关键词 制备 4-羰基鬼臼毒 立体化学 研究 Pdophyllotoxin Oxidation Stereochemistry
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