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Clavilactones是从蘑菇中分离得到的一类天然产物分子,具有良好的抗菌等生物活性,其核心是具有高度环张力的环氧并环丁内酯骨架.中国人民大学化学系李志平课题组通过铁催化烯烃羰基化-过氧化(J.Am.Chem.Soc.2011,133,10756;Tetrahedron Lett.2013,54,6337)、碱催化环氧化以及还原内酯化(Chem.Asian J.2013,8,359),高效高选择性构建了其核心骨架环氧并环丁内酯,成功完成了(±)-Clavilactone A和(±)-Clavilactone B的全合成,首次实现了文献报道结构(±)-Clavilactone D的全合成工作,并指出了分离文献中的结构错误.该研究成果为该类天然产物分子的生物活性研究提供了重要的实验基础.同时,该项研究也为具有环氧并环丁内酯骨架天然产物分子的合成提供了一种新的合成策略.
Clavilactones is a kind of natural product molecule isolated from mushrooms and has good antibacterial and other biological activity, the core of which is epoxycyclobutyrolactone skeleton with high ring tension. Li Zhiping, Department of Chemistry, Renmin University of China, Olefin carbonylation-peroxidation (J. Am. Chem. Soc. 2011, 113, 10756; Tetrahedron Lett. 2013, 54, 6337), base-catalyzed epoxidation and reductive lactonization (Chem. ), The core skeleton of epoxycyclobutyrolactone was constructed with high selectivity and selectivity, and the complete synthesis of (±) -Clavilactone A and (±) -Clavilactone B was successfully completed. The first reported structure of (±) -Clavilactone D, and pointed out the structural errors in the separation of the literature.The results of this study provide an important experimental basis for the study of the biological activity of natural product molecules.At the same time, The synthesis of the natural product molecule of the ester backbone provides a new synthetic strategy.