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

JAN BERGMANN , Christer Löfstedt, Vladimir D. Ivanov, Wittko Francke

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

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-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.

Original languageEnglish
Pages (from-to)3669-3672
Number of pages4
JournalTetrahedron Letters
Volume45
Issue number18
DOIs
StatePublished - 26 Apr 2004

Keywords

  • Bicyclic acetals
  • Caddisflies
  • Communication
  • Insects
  • Trichoptera

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