Skip to content

Research at St Andrews

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

Research output: Contribution to journalArticle

Open Access Status

  • Embargoed (until 20/03/20)


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

School/Research organisations


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
Issue number21
Early online date20 Mar 2019
Publication statusPublished - 24 May 2019

    Research areas

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

Discover related content
Find related publications, people, projects and more using interactive charts.

View graph of relations

Related by author

  1. Unexpected α,α'-difluoroethers from Ag(i)F and N-bromosuccinimide reactions of dibenzo[a,e]cyclooctatetraene

    Fang, Z., Gillatt, R. Z., Slawin, A. M. Z., Cordes, D. B., Carpenter-Warren, C. L. & O'Hagan, D., 11 Dec 2019, In : Chemical Communications. 55, 95, p. 14295-14298 4 p.

    Research output: Contribution to journalArticle

  2. Fluorinated cyclopropanes: Synthesis and chemistry of the aryl α,β,β-trifluorocyclopropane motif

    Thomson, C., Zhang, Q., Al-Maharik, N., Buehl, M., Cordes, D. B., Slawin, A. & O'Hagan, D., 3 Jul 2018, In : Chemical Communications. In press

    Research output: Contribution to journalArticle

  3. Metabolism and hydrophilicity of the polarised ‘Janus face’ all-cis tetrafluorocyclohexyl ring, a candidate motif for drug discovery

    Rodil, A., Bosisio, S., Salah Ayoup, M., Quinn, L., Cordes, D. B., Slawin, A. M. Z., Murphy, C., Michel, J. & O'Hagan, D., 21 Mar 2018, In : Chemical Science. 9, 11, p. 3023-3028

    Research output: Contribution to journalArticle

  4. The synthesis and evaluation of fluoro-, trifluoromethyl, and iodomuscimols as GABA agonists

    Abdul Manan, M. A. F., Cordes, D., Slawin, A., Buehl, M., Liao, V., Chua, H., Chebib, M. & O'Hagan, D., 10 Aug 2017, In : Chemistry - A European Journal. 23, 45, p. 10848-10852 5 p.

    Research output: Contribution to journalArticle

Related by journal

  1. Assessment of the regioselectivity in the condensation reaction of unsymmetrical o-phthaldialdehydes with alanine

    D'Hollander, A. C. A. & Westwood, N. J., 11 Jan 2018, In : Tetrahedron. 74, 2, p. 224-239

    Research output: Contribution to journalArticle

  2. Best practice considerations for using the selectivity factor, s, as a metric for the efficiency of kinetic resolutions

    Greenhalgh, M. D., Taylor, J. E. & Smith, A. D., 20 Sep 2018, In : Tetrahedron. 74, 38, p. 5554-5560 7 p.

    Research output: Contribution to journalArticle

  3. From one to two quaternary centers: ester or nitrile α-alkylation applied to bioactive alkaloids

    Voûte, N., Neal, A., Medda, F., Johnston, C. A., Slawin, A. M. Z. & Westwood, N. J., 8 Nov 2018, In : Tetrahedron. In press

    Research output: Contribution to journalArticle

Related by journal

  1. Tetrahedron (Journal)

    Stuart John Conway (Editor)
    2007 → …

    Activity: Publication peer-review and editorial work typesEditor of research journal

ID: 258305442