Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera)

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• 作者：Bergmann ; Jan ; Lö ; fstedt ; Christer ; Ivanov ; Vladimir D. ; Francke ; Wittko
• 关键词：Bicyclic acetals ; Caddisflies ; Trichoptera ; Insects ; Communication
• 刊名：Tetrahedron Letters
• 出版年：2004
• 出版时间：April 26, 2004
• 年：2004
• 卷：45
• 期：18
• 页码：3669-3672
• 全文大小：266 K

文摘

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-dioxabicyclo[3.2.1]octane, while Glyphotaelius pellucidus produces 1,3-diethyl-4,6-dimethyl-2,7-dioxabicyclo[2.2.1]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.