73264-91-2Relevant articles and documents
Synthetic pheromone compositions
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Page/Page column 6, (2010/11/30)
The present invention provides compounds useful for preparing synthetic pheromone compositions that can be used as attractants or inhibitors of insect species. The compositions are useful in the control of navel orangeworm or meal moth insect pests.
Stereoselective Synthesis of (E)-, (E,Z)-, and (E,E)-Conjugated Dienes via Alkylation of 3-Sulfolenes as the Key Step
Yamada, Sachiko,Ohsawa, Hideto,Suzuki, Takayoshi,Takayama, Hiroaki
, p. 4934 - 4940 (2007/10/02)
A new stereoselective method is presented for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step.Direct alkylation of 3-sulfolene at the 2-position proceeds with good yields when labile sulfolene α-carbanion is generated in the presence of alkyl iodides in THF-HMPA solution at -78 deg C.Alkylation of 2-alkyl-3-sulfolenes gives trans-2,5-dialkyl-3-sulfolenes with 100percent regioselectivity and more than 90percent stereoselectivity.Desulfonylation of trans-3,5-disubstituted 3-sulfolenes is examined in detail, and the conditions to give stereoselectively the corresponding (E,Z)-and (E,E)-conjugated dienes are found.Applying the method, three insect pheromones, (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red bollworm moth, (E,E)-8,10-dodecadien-1-ol, a sex pheromone of the codling moth, and (E,E)-11,13-hexadecadienal, a sex pheromone of the cabbage webworm, are easily synthesized by starting with 3-sulfolene with nearly 100percent stereoselectivity.Synthesis of cis-3,4,5-trisubstituted cyclohexenes using 2-substituted 3-sulfolenes as the diene synthons is also described.
Identification of the Female Sex Pheromone of the Cabbage Webworm
Arai, Koshi,Ando, Tetsu,Sakurai, Akira,Yamada, Hideo,Koshihara, Tatsuo,Takahashi, Nobutaka
, p. 2395 - 2398 (2007/10/02)
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