874461-90-2Relevant academic research and scientific papers
Synthesis of disparlure analogues, using resolution on microcrystalline cellulose triacetate-I
Inkster, James A. H.,Ling, Ivy,Honson, Nicolette S.,Jacquet, Loic,Gries, Regine,Plettner, Erika
, p. 3773 - 3784 (2005)
The gypsy moth, Lymantria dispar, uses a chiral epoxide, (+)-(7R,8S)-2-methyl-7,8-epoxyoctadecane, (+)-disparlure, as its main sex attractant. The moths can detect both enantiomers of disparlure and respond differently to each one. In an effort to understand the structure-activity relationships of the gypsy moth olfactory system, we prepared the analogues of (+)- and (-)-disparlure. The key intermediate in route to the analogues was 2-epoxytridecan-1-ol. Herein we report the resolution of 2-epoxytridecan-1-yl esters on microcrystalline cellulose triacetate and the synthesis of 5-oxa and (5Z)-ene analogues of (+)- and (-)-disparlure. An effort to make 5-aza analogues resulted in the formation of anti-5-(1-hydroxy-1-undecyl)-3-(3-methylbutyl) oxazolidin-2-one. The analogues were tested for their electroantennogram responses and for their ability to bind to pheromone-binding protein 1 (PBP1). We found that the 5-oxa analogues gave strong responses and that the antenna and the PBP1 no longer distinguish the enantiomers of the 5-oxa analogues. The analogues all bound the PBP1 with similar affinity to (-)-disparlure.
