Publications by authors named "Allan C Oehlschlager"

Attraction of Phyllophaga elenas to vaned bucket traps baited with the recently identified female-produced pheromone, L-isoleucine methyl ester (LIME), is efficient. Pheromone-baited vaned buckets with water to retain insects were more effective than buckets without vanes or plastic containers with the sides cut out. Pheromone-baited vaned bucket traps from which water was omitted required the addition of a funnel below the vanes to retain insects.

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Three amino acid-derived compounds were identified in extracts from the pheromone glands of the scarab beetle Phyllophaga elenans, i.e., L-isoleucine methyl ester (LIME), N-formyl L-isoleucine methyl ester (For-LIME), and N-acetyl L-isoleucine methyl ester (Ac-LIME).

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Attraction of Metamasius hemipterus (Oliver) to gallon and bamboo traps baited with insecticide-treated sugarcane, the male-produced pheromone, 4-methyl-5-nonanol, and 2-methyl-4-heptanol is more efficient if ethyl acetate is added. The optimal traps are ground-level gallon traps baited with insecticide-laced sugarcane, pheromone, and ethyl acetate. Capture rates of ground-level gallon traps are doubled by placing an insecticide-laced pad under the trap, but significantly decreased by placing the trap on a stick above ground.

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Synthesis of (+)-disparlure, 1, the sex pheromone of gypsy moth (Lymantria dispar), commenced from cis-vinyl epoxide 4 which was prepared by our asymmetric chloroallylboration in 99% de and 94% ee. Hydroboration of 4 using dicyclohexylborane in THF, followed by sodium perborate oxidation gave a crystalline cis-3,4-epoxy alcohol 3 whose enantiomeric purity was enhanced by recrystallization. Conversion of 3 to (+)-disparlure was via alkylation of the tosylate.

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A new method to generate chiral syn-vinylchlorohydrins and cis-vinyloxiranes is reported. Reaction of (alpha-haloallyl)lithiums with methoxy-9-BBN or Ipc(2)BOMe followed by treatment with BF(3).OEt(2) leads to (Z)-(gamma-haloallyl)boranes which react with aldehydes to yield cis-vinylepoxides (de >/= 90%) upon oxidative workup.

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