Fluorine in pheromones: Synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics
| Autor: | Mingyan Yang, Charlotte S. Teschers, Qingzhi Zhang, Lucas E. Roscoe, Alexandra M. Z. Slawin, Ricardo Callejo, Peter J. Silk, Krista Ryall, Mingan Wang, David B. Cordes, David O'Hagan |
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| Přispěvatelé: | University of St Andrews. School of Chemistry, University of St Andrews. EaSTCHEM, University of St Andrews. Biomedical Sciences Research Complex |
| Rok vydání: | 2019 |
| Předmět: |
Electroantennogram (EAD) analyses
12-Decanolides Stereochemistry chemistry.chemical_element 010402 general chemistry 01 natural sciences Biochemistry chemistry.chemical_compound Emerald ash borer Drug Discovery QD biology Organofluorine chemistry 010405 organic chemistry Organic Chemistry DAS Fluorine containing Insect pheromones QD Chemistry biology.organism_classification 0104 chemical sciences chemistry Sex pheromone Fluorine Pheromone |
| Zdroj: | Tetrahedron. 75:2917-2922 |
| ISSN: | 0040-4020 |
| Popis: | Authors thank the Engineering and Physical Sciences Research Council (EPSRC) for funding and we are grateful to the EPSRC Mass Spectroscopy Service at the University of Swansea for carrying out some of the accurate mass analysis of prepared compounds. 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. Postprint |
| Databáze: | OpenAIRE |
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