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

Bergmann, J ; Löfstedt, Christer LU ; Ivanov, V D and Francke, W (2001) In European Journal of Organic Chemistry 2001(16). p.3175-3179
Abstract
Glands of the 4th and 5th abdominal sternite 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.
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author
; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
European Journal of Organic Chemistry
volume
2001
issue
16
pages
3175 - 3179
publisher
Wiley-VCH Verlag
external identifiers
  • scopus:0034866429
ISSN
1434-193X
DOI
10.1002/1099-0690(200108)2001:16<3175::AID-EJOC3175>3.0.CO;2-4
language
English
LU publication?
yes
id
27dd4275-5be2-479e-b314-5bebd07bb410 (old id 146265)
date added to LUP
2016-04-04 07:31:17
date last changed
2025-10-14 10:42:56
@article{27dd4275-5be2-479e-b314-5bebd07bb410,
  abstract     = {{Glands of the 4th and 5th abdominal sternite 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.}},
  author       = {{Bergmann, J and Löfstedt, Christer and Ivanov, V D and Francke, W}},
  issn         = {{1434-193X}},
  language     = {{eng}},
  number       = {{16}},
  pages        = {{3175--3179}},
  publisher    = {{Wiley-VCH Verlag}},
  series       = {{European Journal of Organic Chemistry}},
  title        = {{Identification and assignment of the absolute configuration of biologically active methyl-branched ketones from limnephilid caddisflies}},
  url          = {{http://dx.doi.org/10.1002/1099-0690(200108)2001:16<3175::AID-EJOC3175>3.0.CO;2-4}},
  doi          = {{10.1002/1099-0690(200108)2001:16<3175::AID-EJOC3175>3.0.CO;2-4}},
  volume       = {{2001}},
  year         = {{2001}},
}