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

Summary, in English

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. (C) 2004 Published by Elsevier Ltd.

• Author: Jan Bergmann; Christer Löfstedt; Vladimir D Ivanov; Wittko Francke
• Department/s: Functional zoology; Pheromone Group
• Publishing year: 2004
• Language: English
• Pages: 3669-3672
• Publication/Series: Tetrahedron Letters
• Volume: 45
• Issue: 18
• Links: http://dx.doi.org/10.1016/j.tetlet.2004.03.024
• Document type: Journal article
• Publisher: Elsevier
• Topic: Zoology; Biological Sciences
• Status: Published
• Research group: Pheromone Group
• ISBN/ISSN/Other: ISSN: 0040-4039