Simple synthesis of mite pheromone beta-acaridial and its analogs in the secretion of Caloglyphus polyphyllae (Acari: Acaridae).
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.
Shimizu
Nobuhiro
N
Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan.
Mori
Naoki
N
Kuwahara
Yasumasa
Y
D000053:Acari / Q000737:chemistry* / Q000502:physiology; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000605:Amino Alcohols / Q000737:chemistry; D000818:Animals; D002849:Chromatography, Gas; D010084:Oxidation-Reduction; D012724:Sex Attractants / Q000138:chemical synthesis / Q000378:metabolism; D013237:Stereoisomerism
D000447:Aldehydes; D000605:Amino Alcohols; D012724:Sex Attractants; C448740:beta-acaridial