Fluorine in pheromones: synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics

Qingzhi Zhang, Charlotte S. Teschers, Ricardo Callejo, Mingyan Yang, Mingan Wang, Peter J. Silk, Krista Ryall, Lucas E. Roscoe, David B. Cordes, Alexandra M.Z. Slawin, David O'Hagan

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

A series of five 12-dodecanolides have been synthesised containing CF2 groups at C5, C6, C7, C8 and in one case a double substitution at C5 & C8, as a strategy to bias the conformational space accessed by these macrocycles, and to assess if the analogues may act as mimetics for 12-decenolide pheromones associated with the Emerald Ash Borer. Accordingly individual syntheses of 5,5-difluoro- 5, 6,6-difluoro- 6, 7,7-difluoro- 7, 8,8-difluoro- 8 and 5,5,8,8-tetrafluoro- 9, 12-decanolides is outlined and X-ray structural data was obtained for three (5, 8 and 9) of these compounds. The structures show clearly that the CF2 groups occupy ‘corner’ locations in the macrocycle consistent with their ability to bias accessible conformations. The fluorine containing 12-dodecanolides all generated an electro-antennogram response in female beetles.
Original languageEnglish
Pages (from-to)2917-2922
JournalTetrahedron
Volume75
Issue number21
Early online date20 Mar 2019
DOIs
Publication statusPublished - 24 May 2019

Keywords

  • Insect pheromones
  • Emerald ash borer
  • Organofluorine chemistry
  • 12-Decanolides
  • Electroantennogram (EAD) analyses

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