96882-97-2Relevant academic research and scientific papers
Pheromone Synthesis, CXXVI. Synthesis and Biological Activity of Four Stereoisomers of 6,10,14-Trimethyl-2-pentadecanol, the Female-Produced Sex Pheromone of Rice Moth (Corcyra cephalonica)
Mori, Kenji,Harada, Hironori,Zagatti, Pierre,Cork, Alan,Hall, David R.
, p. 259 - 267 (2007/10/02)
The synthesis of four stereoisomers of the female-produced sex pheromone of the rice moth (Corcyra cephalonica) was achieved by starting from (R)-2a, (R)- or (S)-3a, and (R)- or (S)-4 and using alkylation of alkyl phenyl sulfones as the coupling reaction.Behavioral bioassy of each isomer revealed (2R,6R,10R)-1a to be eight times more active than a diastereomeric mixture of equal amounts of the eight possible stereoisomers, indicating that (2R,6R,10R)-1a is probably the natural pheromone or at least themajor component of the female blend.Electrophysiological bioassy also confirmed the high activity of (2R,6R,10R)-1a.
SYNTHESIS OF THE ENANTIOMERS OF CIS-2-METHYL-5-HEXANOLIDE, THE MAJOR COMPONENT OF THE SEX PHEROMONE OF THE CARPENTER BEE
Mori, Kenji,Senda, Shuji
, p. 541 - 546 (2007/10/02)
(2R,5S)-2-Methyl-5-hexanolide and its antipode were synthesized in highly optically pure state (98-99percent e.e.) starting from ethyl (S)-lactate and the enantiomers of methyl β-hydroxyisobutyrate.The specific rotations of our samples were D +/- 91.0 -93.5 deg (CHCl3), while the reported values of the samples prepared by resolution or asymmetric synthesis were +/- 64.5-65.6 deg.
