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

D. Geerdink, J. Buter, T.A. van Beek, A.J. Minnaard

Research output: Contribution to journalArticleAcademicpeer-review

7 Citations (Scopus)

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)-4,6,8,10-tetramethyltrideca-2E,4E-dien-1-ol (2), is reported as a contribution to this identification. Catalytic asymmetric conjugate addition of methylmagnesium bromide and stereoselective Horner–Wadsworth–Emmons olefinations are used as the key steps, and 2 was obtained in 16 steps with an overall yield of 4.4%.
Original languageEnglish
Pages (from-to)761-766
JournalBeilstein Journal of Organic Chemistry
Volume10
DOIs
Publication statusPublished - 2014

Keywords

  • mycobacterium-tuberculosis
  • absolute-configuration
  • phthioceranic acid
  • elucidation
  • convergent
  • reductions

Fingerprint Dive into the research topics of 'Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica'. Together they form a unique fingerprint.

  • Cite this