| Synthesis and bioassay of all four stereoisomers of (2E,4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the assignment of the absolute configuration of the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale |
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| 作者姓名： | LIN Guo-Qiang XU Wei-ChuShanghai Institute of Organic Chemistry Chinese Academy of Sciences Shanghai ChinaQI Yun-Tai CHEN Guo-MinShanghai Institute of Entomology Chinese Academy of Sciences Shanghai China |
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| 作者单位： | LIN，Guo-Qiang XU，Wei-ChuShanghai Institute of Organic Chemistry，Chinese Academy of Sciences，Shanghai 200032，ChinaQI，Yun-Tai CHEN，Guo-MinShanghai Institute of Entomology，Chinese Academy of Sciences，Shanghai 200025，China |
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| 基金项目： | supported by the National Natural Science Foundation of China. |
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| 摘 要： | A facile enantioselective synthesis of all four stereoisomers of (2E,4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) is described. The stereochemistry at 6-C and 10-C of 1 was constructed by using optically active citronellal as starting material and by the asymmetric crotylic metal reaction. In the bioassay and field tests, only la, i.e. (6R,10R)-1 was active. The other three isomers 1b (6S,10R), 1c (6R,10S) and 1d (6S,10S) were inactive. Therefore, the naturally occurring pheromone was assigned as (6K,10R)-1.
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Synthesis and bioassay of all four stereoisomers of (2E,4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the assignment of the absolute configuration of the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale |
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| LIN,Guo-Qiang XU,Wei-ChuShanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai ,ChinaQI,Yun-Tai CHEN,Guo-MinShanghai Institute of Entomology,Chinese Academy of Sciences,Shanghai ,China.Synthesis and bioassay of all four stereoisomers of (2E,4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one, the assignment of the absolute configuration of the sex pheromone of Matsucoccus matsumurae Japanese pine bast scale[J].Chinese Journal of Chemistry,1995,13(1):85-94. |
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| Authors: | LIN Guo-Qiang XU Wei-Chu |
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| Institution: | LIN,Guo-Qiang XU,Wei-ChuShanghai Institute of Organic Chemistry,Chinese Academy of Sciences,Shanghai 200032,ChinaQI,Yun-Tai CHEN,Guo-MinShanghai Institute of Entomology,Chinese Academy of Sciences,Shanghai 200025,China |
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| Abstract: | A facile enantioselective synthesis of all four stereoisomers of (2E,4E)-4,6,10,12-tetramethyl-2,4-tridecadien-7-one (1) is described. The stereochemistry at 6-C and 10-C of 1 was constructed by using optically active citronellal as starting material and by the asymmetric crotylic metal reaction. In the bioassay and field tests, only la, i.e. (6R,10R)-1 was active. The other three isomers 1b (6S,10R), 1c (6R,10S) and 1d (6S,10S) were inactive. Therefore, the naturally occurring pheromone was assigned as (6K,10R)-1. |
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| Keywords: | Sex pheromone Japanese pine bast scale Matsuone (2E 4E)-4 6 10 12-tetramethyl-2 4-tridecadien-7-one |
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