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Issue 18, 2020
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Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes

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Abstract

Males of the parasitoid wasp Urolepis rufipes use 2,6-dimethyl-7-octene-1,6-diol as a sex pheromone to attract virgin females. Herein, we determine the absolute configuration of the pheromone to be (2S,6S)-2,6-dimethyl-7-octene-1,6-diol (2S,6S-6) and present a stereoselective synthesis of the natural enantiomer of this new linalool derivative. In addition, we show that female wasps respond to the natural 2S,6S-6 stereoisomer while 2R,6S-6 is behaviorally inactive.

Graphical abstract: Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes

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Article information


Submitted
24 Mar 2020
Accepted
08 Apr 2020
First published
08 Apr 2020

Org. Biomol. Chem., 2020,18, 3463-3465
Article type
Communication

Enantioselective synthesis and determination of the absolute configuration of the male sex pheromone of the parasitoid wasp Urolepis rufipes

K. Melnik, C. Grimm, J. Wittbrodt, J. Ruther and S. Schulz, Org. Biomol. Chem., 2020, 18, 3463
DOI: 10.1039/D0OB00614A

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