Simple Synthesis of Mite Pheromone β-Acaridial and Its Analogs in the Secretion of Caloglyphus polyphyllae (Acari : Acaridae)(Organic Chemistry)

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A simple synthesis of β-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, β-acariolal 8, was also prepared in a 63% yield by oxidation of the intermediate, β-acaridiol [(E) -7], with pyridinium dichromate (PDC). This synthetic route also gave β- (Z) -acaridiol [(Z) -7] by using a Z-selective base in the Wittig reaction. (Z) -7 was oxidized to give a new monoterpene, β- (Z) -acaridial [(Z) -1], which was detected as a trace component in the secretion of Caloglyphus polyphyllae, together with 8.
社団法人日本農芸化学会の論文
2003-08-23