| Title: | Simple synthesis of mite pheromone beta-acaridial and its analogs in the secretion of Caloglyphus polyphyllae (Acari: Acaridae) |
| Author(s): | Shimizu N; Mori N; Kuwahara Y; |
| Address: | "Laboratory of Chemical Ecology, Division of Applied Life Sciences, Graduate School of Agriculture, Kyoto University, Sakyo-ku, Kyoto 606-8502, Japan" |
| Journal Title: | Biosci Biotechnol Biochem |
| ISSN/ISBN: | 0916-8451 (Print) 0916-8451 (Linking) |
| 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" |
| Keywords: | "Acari/*chemistry/physiology Aldehydes/*chemical synthesis/chemistry Amino Alcohols/chemistry Animals Chromatography, Gas Oxidation-Reduction Sex Attractants/chemical synthesis/metabolism Stereoisomerism;" |
| Notes: | "MedlineShimizu, Nobuhiro Mori, Naoki Kuwahara, Yasumasa eng Research Support, Non-U.S. Gov't England 2003/09/03 Biosci Biotechnol Biochem. 2003 Aug; 67(8):1732-6. doi: 10.1271/bbb.67.1732" |
