高等有机化学（朱钢国）第七章 有机合成路线设计（一）.pptVIP

第一节 有机合成的意义 有机合成的内涵 通过设计完成目标分子，包括天然产物分子及理论上有兴趣的有特殊结构的分子的全合成，有时还用于明证目标化合物的结构，制备天然产物的衍生物，开发出更好的生物、物理和化学性能的化合物。 提供足够数量的有用的目标化合物以弥补天然资源的不足。 发现新的有机反应、试剂及合成设计策略和合成技术，发展新的反应理论。 第二节 有机合成设计基础知识 理想的保护基 上保护容易，去保护也容易； 上保护、去保护时不影响其它官能团； 官能团保护后应该具有适当的稳定性。 常见保护基举例 甲基醚(ROCH3) 甲氧基甲基醚 烯丙基醚 苄基醚 * 有机合成是“无中生有”正如有机合成的先师Woodward教授所说：“在有机合成中充满着兴奋、冒险、挑战和艺术”。 1.二战之前 Selected total syntheses of natural products from 1901-1939 松油醇 樟脑 托品酮 氯高铁血红素 盐酸吡哆醇 马萘雌〔甾〕酮 2. The Woodward Era Robert Burns Woodward (1917-1979) is generally recognized as the leading organic chemist of the twentieth century. He and his coworkers determined the structures of biologically active natural products, developed theoretical rules for predicting the outcomes of organic reactions, and synthesized some of the most complex molecules known to humans. In 1965 Woodward received the Nobel Prize in chemistry for his outstanding achievements in the art of organic synthesis. Selected syntheses by the Woodward Group (1944-1981) 奎宁 棒曲霉素 红霉素A肟 头孢菌素C 叶绿素a 利血平 青霉烯 小皮伞菌酸 秋水仙碱  羊毛甾醇 士的宁 可的松 麦角酸 3. The Coery Era Elias James Corey (born July 12, 1928) is an American organic chemist. In 1990 he won the Nobel Prize in Chemistry for his development of the theory and methodology of organic synthesis, specifically retrosynthetic analysis.Regarded by many as one of the greatest living chemists, he has developed numerous synthetic reagents, methodologies, and has advanced the science of organic synthesis considerably. / 贡献： 试剂： PCC (pyridinium chlorochromate) also referred to as the Corey-Suggs reagent, and PDC (pyridinium dichromate): widely used for the oxidation of alcohols to aldehydes. t-Butyldimethylsilyl ether (TBDMS), Triisopropylsilyl ether (TIPS), and Methoxyethoxymethyl (MEM): popular alcohol protecting groups. 方法学： Corey-Bakshi-Shibata reduction Corey-Fuchs reaction Corey–Kim oxidation Corey-Winter olefin synthesis Corey-House-Posner-Whitesides reaction Johnson-Corey-Chaykovsky reaction Corey-Seebach reaction 全合成 提出