Citation: Qing Cui, Lin Kang, Hai Shen Yang, Xiao Hua Xu. The new synthesis of sesquiterpenoids 10-bromo-α-chamigrene[J]. Chinese Chemical Letters, ;2009, 20(5): 554-556. doi: 10.1016/j.cclet.2009.01.029 shu

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

State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Received Date: 20 October 2008

Fund Project: We thank the National Natural Science Foundation of China (No.20421202) for financial support.

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.
- 10-Bromo-α-chamigrene,
- Halogenated sesquiterpenoids,
- Carbonyl coupling,
- Synthesis
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