- Regio- and stereochemical study of sex pheromone of pine sawfly; Diprion nipponica
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Regio- and stereoisomers of 1,2,ω-trimethyldecyl propionate (ω = 5-9) were prepared from stereochemically pure chiral building blocks as sex pheromone candidates of a pine sawfly; Diprion nipponica. Among the synthesized candidates, (1S,2R,8S)-1,2,8-trimethyldecyl propionate was found to be the sex pheromone of D. nipponica, based on compatibility of its GC-MS data with that of the extract of females, and its significantly high pheromone activity in a field bioassay. The field bioassay of the synthesized compounds also revealed that (1S,2R,SR)-1,2,8-trimethyldecyl propionate, (1S,2R,7S)-1,2,7-trimethyldecyl propionate, and (1S,2R,6S)-1,2,6-trimethyldecyl propionate could attract male sawflies to some extent as pheromone mimics.
- Tai, Akira,Syouno, Emi,Tanaka, Kazuki,Fujita, Morifumi,Sugimura, Takashi,Higashiura, Yasutomo,Kakizaki, Masashi,Hara, Hideho,Naito, Tikahiko
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p. 111 - 121
(2007/10/03)
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- A facile synthesis of (S)-trogodermal
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A simple route for the synthesis of (S)-(Z)- and (S)-(E)-14-methyloctadec-8-en-1-al (Ia and Ib) has been developed.The achiral acetylene (9) is alkylated with the chiron bromide (S)-5 in the presence of BuLi as the base to give 10.This on subsequent functionalisation furnishes both Ia and Ib.
- Chattopadhay, S.,Mamdapur, V. R.,Chadha, M. S.
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p. 848 - 849
(2007/10/02)
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