Stereoselective synthesis of 11(E)-tetradecen-1-yl acetate-Sex pheromone of sod webworm (Loxostege sticticalis)
On the basic of Claisen rearrangement using orthoesters we carried out stereoselective synthesis of 11(E)-tetradecen-1-yl acetate, a sex pheromone of sod webworm (Loxostege sticticalis), which is a specially dangerous pests of crops.
Shakhmaev,Ishbaeva,Shayakhmetova
p. 1171 - 1174
(2011/05/04)
Insect sex pheromones. Stereospecific syntheses of few lepidoptera pheromones containing (E)-Alkene moiety
-
Vig,Kad,Sabharwal,Dogra,Sharma
p. 233 - 235
(2007/10/02)
SYNTHESIS OF(E) AND (Z) ALKENES VIA PALLADIUM OR NICKEL-CATALYZED REACTION OF VINYL CHLORIDES WITH GRIGNARD REAGENTS.
We herein described (i) a useful transformation of (E) and (Z) vinyl chlorides into E (and Z) olefins and (ii) an efficient preparation of monoenic alcohols or acetates and its application to insect pheromones.
Ratovelomanana, Victorin,Linstrumelle, Gerard
p. 179 - 188
(2007/10/02)
Synthesis of (E)-11-Tetradecen-1-ol
Protection of alcoholic function of the alcohol (II) as its tetrahydropyranyl ether gives III which on hydroboration-oxidation reaction affords 11-tetrahydropyranyloxyundecanol (IV).Oxidation of IV with pyridinium chlorochromate in anhyd. methylene chloride yields the corresponding aldehyde (V) which when subjected to modified Wittig reaction with ethyl diethylphosphonoacetate furnishes ethyl 13-tetrahydropyranyloxy-2(E)-tridecenoate (VI).LAH reduction of VI in dry benzene affords the alcohol (VII) in good yield.Conversion of the alcohol (VII) into the corresponding mesylate (VIII) with mesyl chloride/triethylamine in dry methylene chloride at 0 deg C, followed by reaction with dimethyl lithiocuprate at -10 deg C under nitrogen atmosphere provides the pyranyl ether (IX) which upon removal of the protective group with conc.HCl in methanol gives the naturally occurring sex pheromone (E)-11-tetradecen-1-ol (I).
Vig, O. P.,Sharma, M. L.,Verma, N. K.,Malik, Neera
p. 581 - 582
(2007/10/02)
Pheromones XXVIII. A stereoselective synthesis of (E)-olefinic sex pheromones of moths
-
Canevet,Roeder,Vostrowsky,Bestmann
p. 1115 - 1120
(2007/10/02)
More Articles about upstream products of 57586-92-2