Synthesis of (3E, 5Z)-3,5-dodecadienylacetate, the sex pheromone of Phtheochroa cranaodes (Lepidoptera: Tortricidae.
(3E, 5Z)-3,5-Dodecadienyl acetate, the female sex pheromone of Phtheochroa cranaodes, was regio and stereo-selectively synthesized from 1-octyne and (E)-4bromo-3-buten-1-ol by using Pd(PPh3)4, CuI and piperidine to afford the enyne (5). Further elaboration afforded the target pheromone. The synthetic pheromone was identified with the natural product by its MS and IR, data GLC retention time and biological activity.
Yadav
J S
JS
Pheromone Laboratory, Organic Division-I, Indian Institute of Chemical Technology, Hyderabad, India. yadav@iict.ap.nic.in
Reddy
E J
EJ
D000085:Acetates / Q000138:chemical synthesis*; D000818:Animals; D001938:Brazil; D002846:Chromatography, Affinity; D007851:Dodecanol / Q000031:analogs & derivatives; D005260:Female; D013058:Mass Spectrometry; D008956:Models, Chemical; D009036:Moths / Q000502:physiology*; D012724:Sex Attractants / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
C419347:3,5-dodecadienyl acetate; D000085:Acetates; D012724:Sex Attractants; D007851:Dodecanol