Identification and assignment of the absolute configuration of biologically active methyl-branched ketones from limnephilid caddis flies

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

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

Glands of the 4th and 5th abdominal stemite of the caddis flies Potamophylax latipennis, Potamophylax cingulatus, and Glyphotaelius pellucidus contain (S)-4-methyl-3-heptanone (4a), (4S,6S)-4,6-dimethyl-3-octanone (4b), and (4S,6S)-4,6-dimethyl-3-nonanone (4c). As shown by gas chromatography coupled with electrophysiological recordings, these ketones elicit a strong response in the insects' antennae. The structural assignment of the compounds was achieved on the basis of mass spectra, enantioselective synthesis, and gas chromatography on a chiral stationary phase.

Original languageEnglish
Pages (from-to)3175-3179
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number16
DOIs
StatePublished - 1 Jan 2001

Keywords

  • Asymmetric synthesis
  • Caddis flies
  • Ketones
  • Natural products
  • Structure elucidation

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