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

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Zhang_2019_Tetrahedron_Fluorine_AAM.pdf (733.9Kb)
Date
24/05/2019
Author
Zhang, Qingzhi
Teschers, Charlotte S.
Callejo, Ricardo
Yang, Mingyan
Wang, Mingan
Silk, Peter J.
Ryall, Krista
Roscoe, Lucas E.
Cordes, David B.
Slawin, Alexandra M.Z.
O'Hagan, David
Keywords
Insect pheromones
Emerald ash borer
Organofluorine chemistry
12-Decanolides
Electroantennogram (EAD) analyses
QD Chemistry
DAS
Metadata
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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.
Citation
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
Publication
Tetrahedron
Status
Peer reviewed
DOI
https://doi.org/10.1016/j.tet.2019.03.025
ISSN
0040-4020
Type
Journal article
Rights
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
Description
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.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/19685

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