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

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Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera). / Bergmann, Jan; Löfstedt, Christer; Ivanov, Vladimir D; Francke, Wittko.

In: Tetrahedron Letters, Vol. 45, No. 18, 2004, p. 3669-3672.

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Bergmann, Jan ; Löfstedt, Christer ; Ivanov, Vladimir D ; Francke, Wittko. / Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera). In: Tetrahedron Letters. 2004 ; Vol. 45, No. 18. pp. 3669-3672.

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TY - JOUR

T1 - Identification and synthesis of new bicyclic acetals from caddisflies (Trichoptera)

AU - Bergmann, Jan

AU - Löfstedt, Christer

AU - Ivanov, Vladimir D

AU - Francke, Wittko

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

U2 - 10.1016/j.tetlet.2004.03.024

DO - 10.1016/j.tetlet.2004.03.024

M3 - Article

VL - 45

SP - 3669

EP - 3672

JO - Tetrahedron Letters

T2 - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 18

ER -