104104-38-3Relevant 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.
, 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.
Defense Mechanisms of Arthropods. 84. Synthesis of (-)-α-Necrodol and (-)-β-Necrodol: Novel Cyclopentanoid Terpenes from a Carrion Beetle
Jacobs, Robert T.,Feutrill, Geoffrey I.,Meinwald, Jerrold
, p. 4051 - 4062 (2007/10/02)
Syntheses of (-)-α-necrodol (1) and (-)-β-necrodol (2) from (+)-phenylcamphoric acid (7a) are described.In addition, several related compounds, (+)-epi-α-necxrodol (3), (+)-epi-β-necrodol (4), and (+)-γ-necrodol (5), have been prepared.The absolute configuration of natural α-necrodol has been established as 3R,5R by comparison of its (+)-α-methoxy-α-(trifluoromethyl)phenylacetyl ester with the ester derived from synthetic 1.
