| Title: | Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity |
| Author(s): | Dawson GW; Mudd A; Pickett JA; Pile MM; Wadhams LJ; |
| Address: | "AFRC Institute of Arable Crops Research, Rothamsted Experimental Station, AL5 2JQ, Harpenden, Hertfordshire, UK" |
| ISSN/ISBN: | 0098-0331 (Print) 0098-0331 (Linking) |
| Abstract: | "A simple three-step synthesis is described for 6-acetoxy-5-hexadecanolide, the oviposition pheromone of the mosquitoCulex quinquefasciatus Say and others in that genus. An aldol condensation between 1-trimethylsilyloxycyclopent-1-ene and undecanal, followed by Baeyer-Villiger ring expansion and acetylation, gave the required compound as a 1ratio1 mixture of diastereoisomers in high overall yield (>80%). This synthetic approach is readily adapted for synthesis of analogs. The heptadecafluoro compound, in which then-octyl group is replaced by perfluorooctyl, retained high biological activity" |
| Notes: | "PubMed-not-MEDLINEDawson, G W Mudd, A Pickett, J A Pile, M M Wadhams, L J eng 1990/06/01 J Chem Ecol. 1990 Jun; 16(6):1779-89. doi: 10.1007/BF01020494" |
