| Title: | Fluorinated analogs of aldehyde components of boll weevil pheromone : Synthesis and biological activity |
| Author(s): | Prestwich GD; Sun WC; Dickens JC; |
| Address: | "Department of Chemistry, State University of New York, 11794-3400, Stony Brook, New York" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| Abstract: | "Analogs of the two geometrical isomers of the dimethylcyclohexylidene acetaldehyde component of the pheromone of the boll weevilAnthonomus grandis were synthesized in which the alpha-vinylic proton or the aldehydic proton were replaced by fluorine. These isosteric substitutions substantially alter charge distribution and reactivity of the enal system, as documented by spectroscopic changes and changes in reactivity. The electrophysiological activity of the (E)- and (Z)-acyl fluorides is two orders of magnitude lower than that of the natural aldehyde. In contrast, the EAG response of female antennae to the (E)- and (Z)-alpha-fluoro compounds show that the thresholds are quite similar to (and in one isomer lower than) those of the natural aldehyde isomers" |
| Notes: | "PubMed-not-MEDLINEPrestwich, G D Sun, W C Dickens, J C eng 1988/05/01 J Chem Ecol. 1988 May; 14(5):1427-39. doi: 10.1007/BF01020146" |
