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Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera)
Authors:Jan Bergmann  Vladimir D Ivanov
Institution:a Institute of Organic Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146 Hamburg, Germany
b Department of Ecology, Ecology Building, Lund University, Sölvegatan 37, SE-223 62 Lund, Sweden
c Department of Entomology, St. Petersburg State University, Universitetskaya nab. 7/9, RU-199034 St. Petersburg, Russia
Abstract:As shown by synthesis and enantioselective gas chromatography, males and females of the caddisfly species Potamophylax latipennis and Potamophylax cingulatus produce (1R,3S,5S,7S)-1-ethyl-3,5,7-trimethyl-2,8-dioxabicyclo3.2.1]octane, while Glyphotaelius pellucidus produces 1,3-diethyl-4,6-dimethyl-2,7-dioxabicyclo2.2.1]heptane, having either the (1S,3S,4R,6S) or (1R,3R,4S,6S)-configuration. As shown by electrophysiological investigations, the compounds are perceived by the antennae of both sexes.
Keywords:Bicyclic acetals  Caddisflies  Trichoptera  Insects  Communication
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