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

Bergmann, Jan; Löfstedt, Christer LU ; Ivanov, Vladimir D and Francke, Wittko (2004) In Tetrahedron Letters 45(18). p.3669-3672
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. (C) 2004 Published by Elsevier Ltd.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Tetrahedron Letters
volume
45
issue
18
pages
3669 - 3672
publisher
Elsevier
external identifiers
  • wos:000221022500031
  • scopus:1842686316
ISSN
0040-4039
DOI
10.1016/j.tetlet.2004.03.024
language
English
LU publication?
yes
id
31ea7ee9-f483-4592-944b-e8b7bd36d752 (old id 146194)
date added to LUP
2007-06-27 09:01:13
date last changed
2017-01-01 07:25:18
@article{31ea7ee9-f483-4592-944b-e8b7bd36d752,
  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. (C) 2004 Published by Elsevier Ltd.},
  author       = {Bergmann, Jan and Löfstedt, Christer and Ivanov, Vladimir D and Francke, Wittko},
  issn         = {0040-4039},
  language     = {eng},
  number       = {18},
  pages        = {3669--3672},
  publisher    = {Elsevier},
  series       = {Tetrahedron Letters},
  title        = {Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera)},
  url          = {http://dx.doi.org/10.1016/j.tetlet.2004.03.024},
  volume       = {45},
  year         = {2004},
}