Beilstein J. Org. Chem.2014,10, 767–773, doi:10.3762/bjoc.10.72
Wageningen, The Netherlands Laboratory of Entomology, Wageningen University, P.O. Box 8031, 6700 EH Wageningen, The Netherlands 10.3762/bjoc.10.72 Abstract Females of the parasitoid wasp Trichogrammaturkestanica produce the putative polydeoxypropionates (2E,4E,6S,8S,10S)-4,6,8,10-tetramethyltrideca-2,4
about (volatile) semiochemicals playing a role in intraspecific communication [7][8][9][10][11].
Based on bioassays with Trichogrammaturkestanica and extensive analytical investigations, two female-specific volatile compounds have been described as possible pheromone components and were tentatively
Trichogrammaturkestanica, as did the extract of females [12].
Published 70 eV EI mass spectra of the naturally occurring compounds A and B [12].
Synthesis of tetramethyltrideca-2,4-dienes 8, 14 and 15. Conditions: a: LiAlH4, Et2O, −30 °C to rt, 12 h; b: 1) NaH, THF, −20 °C to rt 1 h; 2) TBDMSCl (1 equiv), rt
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Graphical Abstract
Figure 1:
Published 70 eV EI mass spectra of the naturally occurring compounds A and B [12].
Beilstein J. Org. Chem.2014,10, 761–766, doi:10.3762/bjoc.10.71
Wageningen, The Netherlands 10.3762/bjoc.10.71 Abstract Virgin females of the parasitoid wasp Trichogrammaturkestanica produce minute amounts of a sex pheromone, the identity of which has not been fully established. The enantioselective synthesis of a putative component of this pheromone, (6S,8S,10S
of 4.4%.
Keywords: asymmetric catalysis; copper; deoxypropionates; natural products; sex pheromone; Trichogrammaturkestanica; Introduction
Communication by means of pheromones is common in many animal species. For instance, many insects secrete air-borne volatiles to attract a mate for generating
offspring [1][2]. In 2005, one of us reported the isolation and partial characterization of the putative sex pheromone of Trichogrammaturkestanica, a parasitoid wasp [3]. These wasps, belonging to the large Trichogrammatidae family, are minute in size (0.5 mm, 8 µg adult weight) as well as morphologically
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Graphical Abstract
Figure 1:
Originally proposed structures A and B and revised structures 1 and 2 of putative sex pheromone com...