Structure elucidation of female-specific volatiles released by the parasitoid wasp Trichogramma turkestanica (Hymenoptera: Trichogrammatidae)

• Armin Tröger,
• Teris A. van Beek,
• Martinus E. Huigens,
• Isabel M. M. S. Silva,
• Maarten A. Posthumus and
• Wittko Francke

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 Trichogramma turkestanica 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 Trichogramma turkestanica and extensive analytical investigations, two female-specific volatile compounds have been described as possible pheromone components and were tentatively

• Trichogramma turkestanica, 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

Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

• Danny Geerdink,
• Jeffrey Buter,
• Teris A. van Beek and
• Adriaan J. Minnaard

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 Trichogramma turkestanica 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; Trichogramma turkestanica; 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 Trichogramma turkestanica, 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