TY - JOUR
T1 - Identification and assignment of the absolute configuration of biologically active methyl-branched ketones from limnephilid caddis flies
AU - Bergmann, Jan
AU - Löfstedt, Christer
AU - Ivanov, Vladimir D.
AU - Francke, Wittko
PY - 2001
Y1 - 2001
N2 - 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.
AB - 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.
KW - Asymmetric synthesis
KW - Caddis flies
KW - Ketones
KW - Natural products
KW - Structure elucidation
UR - http://www.scopus.com/inward/record.url?scp=0034866429&partnerID=8YFLogxK
U2 - 10.1002/1099-0690(200108)2001:16<3175::AID-EJOC3175>3.0.CO;2-4
DO - 10.1002/1099-0690(200108)2001:16<3175::AID-EJOC3175>3.0.CO;2-4
M3 - Article
AN - SCOPUS:0034866429
SN - 1434-193X
SP - 3175
EP - 3179
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 16
ER -