Fluorine in pheromones : synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics
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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.
Zhang , Q , Teschers , C S , Callejo , R , Yang , M , Wang , M , Silk , P J , Ryall , K , Roscoe , L E , Cordes , D B , Slawin , A M Z & O'Hagan , D 2019 , ' Fluorine in pheromones : synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics ' , Tetrahedron , vol. 75 , no. 21 , pp. 2917-2922 . https://doi.org/10.1016/j.tet.2019.03.025
Copyright © 2019 Published by Elsevier Ltd. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1016/j.tet.2019.03.025
DescriptionAuthors 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.
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