多烯环化反应及其在天然产物全合成中的研究进展  

Progress in Polyene Cyclization Reaction and Its Application in Total Synthesis of Natural Products

作　　者：康亮亮 彭碧 曹盼盼 何述钟 KANG Liangliang;PENG Bi;CAO Panpan;HE Shuzhong(School of Pharmaceutical Sciences,Guizhou University,Guiyang 550025,China;Synthetic Drug Engineering Laboratory of Guizhou Province,Guiyang 550025,China)

机构地区：[1]贵州大学药学院,贵州贵阳550025 [2]贵州省合成药物工程实验室,贵州贵阳550025

出　　处：《化学与粘合》2024年第2期175-178,共4页Chemistry and Adhesion

基　　金：国家自然科学基金项目:环氧型taccalonolides的全合成研究(编号:21861010)。

摘　　要：多烯环化反应是有机合成中一类重要的环化反应,具有高效、简单易行等特点,被广泛应用于医疗领域、天然产物和化工研究中。但当环化反应的环数增多时,会出现较低回率现象。为此,阐述了多烯环化反应及其在天然产物全合成中的研究进展。分析多烯环化反应原理,使用多个碳原子构建环状结构,通过环化反应使得含有多烯或者单烯的混合物转变成链烯结构存在差异的芳香烃。多烯环化反应过程中需要使用金属催化或者非金属催化,金属催化能够保证所生成化合物的稳定性,非金属催化则需要借助高温或者光照才能实现。锰催化多烯环化反应在天然产物全合成中,受到醋酸锰(Ⅲ)影响自由基出现多烯串联环化反应,能够推动生成奥利霉素和雷公藤素,在医疗领域发挥重要作用。烯类化合物在天然反应全合成中,乙酸作用下调聚1,3-丁二烯,经过水解之后能够生成松茸醇。将多烯环化反应应用于角鲨烯衍生聚醚合成中,能够获得较高回率,合成效果较好。Polyene cyclization is an important type of cyclization reaction in organic synthesis,characterized by high efficiency,simplicity,and ease of operation.It is widely used in the medical field,natural products,and chemical research.But when the number of cycles in the cyclization reaction increases,a lower recovery rate will occur.The research progress in polyene cyclization reaction and its application in the total synthesis of natural products is elaborated.The principle of polyene cyclization reaction is analyzed,multiple carbon atoms are used to construct a cyclic structure,and through the cyclization reaction,the polyene or monoene contained mixture converts into aromatic hydrocarbons with varying alkene structures.In the process of polyene cyclization reaction,the metal catalysis or non-metallic catalysis is required.The metal catalysis can ensure the stability of the generated compounds,however the non-metallic catalysis requires the use of high temperature or illumination to achieve.Manganese catalyzed polyene cyclization reaction in the total synthesis of natural products is influenced by manganese acetate(III) to form polyene series cyclization reaction,which can promote the generation of oridamycins and triptolide,playing an important role in the medical field.In the natural synthesis of olefin compounds,the acetic acid downregulates poly(1,3-butadiene),and after hydrolysis,it can generate matsutake alcohol.The application of polyene cy-clization reaction in the synthesis of squalene derived polyethers can achieve high recovery and good synthesis results.

关 键 词：多烯环化反应 天然产物 全合成 金属催化 醋酸锰(Ⅲ) 雷公藤素 

分 类 号：R978[医药卫生—药品]