17790-74-8Relevant articles and documents
Synthesis and bioassay of racemic and chiral trans -α-Necrodyl Isobutyrate, the sex pheromone of the grape mealybug pseudococcus maritimus
Zou, Yunfan,Daane, Kent M.,Bentley, Walt J.,Millar, Jocelyn G.
experimental part, p. 4977 - 4982 (2011/07/31)
A concise synthesis of the racemic form of the female-produced pheromone of the grape mealybug was developed. The synthesis was readily adapted to production of both enantiomers of the pheromone via lipase-catalyzed kinetic resolution of an intermediate in the synthesis. Replicated field trials revealed that, contrary to a preliminary report, the (R,R)- rather than the (S,S)-enantiomer is the attractive stereoisomer. Lithium aluminum hydride reduction of the insect-produced compound to α-necrodol followed by analysis on a chiral stationary phase GC column showed that the insect-produced material was actually an 85:15 mixture of the (R,R)- and (S,S)-enantiomers. The racemic form of the pheromone was highly attractive to male mealybugs, and in one of two field bioassays, the racemic material was significantly more attractive than the pure (R,R)-enantiomer, suggesting that the (S,S)-enantiomer might act synergistically.
-Annulation using Allylidene(triphenyl)phosphoranes: a One-Step Synthesis of Cyclopentadienes
Hatanaka, Minoru,Himeda, Yuichiro,Ueda, Ikuo
, p. 2269 - 2274 (2007/10/02)
A convenient method for the synthesis of substituted cyclopentadienes has been developed using allylidene(triphenyl)phosphoranes. (3-Ethoxycarbonyl-2-substituted-2-propenylidene)triphenylphosphoranes 1 reacted with α-halogenoketones under very mild condit