Simple synthesis of mite pheromone beta-acaridial and its analogs in the secretion of Caloglyphus polyphyllae (Acari: Acaridae) |
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Authors: | Shimizu Nobuhiro Mori Naoki Kuwahara Yasumasa |
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Institution: | Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan. |
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Abstract: | A simple synthesis of beta-acaridial (E)-1], the active principle of the sex, alarm and aggregation pheromone among astigmatid mites, was achieved in 5 steps from 1,2,4-butanetriol 2 in a 19% overall yield. Its analog, beta-acariolal 8, was also prepared in a 63% yield by oxidation of the intermediate, beta-acaridiol (E)-7], with pyridinium dichromate (PDC). This synthetic route also gave beta-(Z)-acaridiol (Z)-7] by using a Z-selective base in the Wittig reaction. (Z)-7 was oxidized to give a new monoterpene, beta-(Z)-acaridial (Z)-1], which was detected as a trace component in the secretion of Caloglyphus polyphyllae, together with 8. |
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