引用本文:
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
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
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
The new synthesis of sesquiterpenoids 10-bromo-α-chamigrene
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.
English
The new synthesis of sesquiterpenoids 10-bromo-α-chamigrene
Abstract:
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.
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Key words:
- 10-Bromo-α-chamigrene
- / Halogenated sesquiterpenoids
- / Carbonyl coupling
- / Synthesis
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