The new synthesis of sesquiterpenoids 10-bromo-α-chamigrene  

作　　者：Qing Cui Lin Kang Hai Shen Yang Xiao Hua Xu 

机构地区：[1]State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

出　　处：《Chinese Chemical Letters》2009年第5期554-556,共3页中国化学快报（英文版）

基　　金：the National Natural Science Foundation of China(No.20421202)for financial support.

摘　　要：The new synthesis of 10-bromo-α-chamigrene was achieved as follows; 6-methyl-5-heptene-2-one was transformed into corresponding thioacetals, and then successively treated with Cp2Ti（P（OEt）3）2. The intermediate reacted with mono-ketal of cyclohexane-1,4-dione, and gave the carbonyl coupling product. It was then transformed into the key intermediate γ-bisabolene via deketalization, Grignard reaction, dehydration and then furnished the target molecule by polyene cyclization, with total yield 2%. All structures were confirmed by ^1H NMR and ^13C NMR. The final compound was confirmed by ^1H NMR, ^13C NMR and MS.The new synthesis of 10-bromo-α-chamigrene was achieved as follows; 6-methyl-5-heptene-2-one was transformed into corresponding thioacetals, and then successively treated with Cp2Ti（P（OEt）3）2. The intermediate reacted with mono-ketal of cyclohexane-1,4-dione, and gave the carbonyl coupling product. It was then transformed into the key intermediate γ-bisabolene via deketalization, Grignard reaction, dehydration and then furnished the target molecule by polyene cyclization, with total yield 2%. All structures were confirmed by ^1H NMR and ^13C NMR. The final compound was confirmed by ^1H NMR, ^13C NMR and MS.

关 键 词：10-Bromo-α-chamigrene Halogenated sesquiterpenoids Carbonyl coupling Synthesis 

分 类 号：O641.4[理学—物理化学] TQ467.95[理学—化学]