Synthesis of the Four Stereoisomers of 7-Acetoxy-15-methylnonacosane, a Component of the Female Sex Pheromone of the Screwworm Fly, Cochliomyia hominivoraxPheromone Synthesis, Part 227. For Part 226, see Muto, S., Bando, M., and Mori, K., Eur. J. Org. Chem., 1946--1952 (2004)
نویسندگان
چکیده
Insect Pheromone and Traps Division, Fuji Flavor Co., Ltd., Midorigaoka 3-5-8, Hamura-shi, Tokyo 205-8503, Japan Graduate School of Life Sciences, Tohoku University, Tsutsumidori-Amamiya 1-1, Aoba-ku, Sendai 981-8555, Japan U.S. Department of Agriculture, Agricultural Research Service, Midwest Livestock Insect Research Unit, Lincoln, Nebraska 68583, U.S.A. U.S. Department of Agriculture, Agricultural Research Service, Center for Medical, Agricultural and Veterinary Entomology, P.O. Box 14565, Gainesville, Florida 32611, U.S.A.
منابع مشابه
Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax.
The four stereoisomers of 7-acetoxy-15-methylnonacosane (1), a component of the female sex pheromone of the New World screwworm fly (Cochliomyia hominivorax) were synthesized. The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17-methyl-1-trimethylsilylpe...
متن کاملDetermination by HPLC fluorescence analysis of the natural enantiomers of sex pheromones in the New World screwworm fly, Cochliomyia hominivorax.
Bioassays of six racemic synthesized candidate sex pheromone compounds against male New World screwworm Cochliomyia hominivorax (Coquerel) flies showed that the most potent bioactivity was found with 6-acetoxy-19-methylnonacosane and 7-acetoxy-15-methylnonacosane compared with four other isomeric acetoxy nonacosanes and a larger aliphatic ketone. As all these methyl-branched compounds have two ...
متن کاملCandidate sex pheromones of the New World screwworm Cochliomyia hominivorax.
Five novel homologous acetate derivatives of long-chain secondary alcohols and a related ketone were tested for their efficacy as contact mating stimulants for Cochliomyia hominivorax Coquerel (Diptera: Calliphoridae). Full copulatory behaviour at a high percentage was found in tests with racemic 6-acetoxy-19-methylnonacosane at 2.5-20 microg using fertile males from three strains. Males of two...
متن کاملNew Synthesis of the (3Z,6Z,9S,10R)-Isomers of 9,10-Epoxy-3,6-henicosadiene and 9,10-Epoxy-1,3,6-henicosatriene, Pheromone Components of the Female Fall Webworm Moth, Hyphantria cuneaPheromone Synthesis, Part 230. For Part 229, see Mori, K., Eur. J. Org. Chem., in press
(3Z,6Z,9S,10R)-9,10-Epoxy-3,6-henicosadiene (1) and (3Z,6Z,9S,10R)-9,10-epoxy-1,3,6-henicosatriene (5), pheromone components of the female fall webworm moth (Hyphantria cunea Drury), were synthesized by starting from (2S,3R)-2,3-epoxy-4-t-butyldimethylsilyloxy-1-butanol (8). Epoxide 8 was prepared by employing lipase-catalyzed asymmetric acetylation of ( )-8 as the key optical resolution step.
متن کاملNew Syntheses of 1,7-Dimethylnonyl Propanoate, the Western Corn Rootworm Pheromone, in Four Different Ways via Cross Metathesis, Alkylation and Coupling ReactionsPheromone Synthesis, Part 242. See ref.1 for Part 241
A mixture of the four stereoisomers of 1,7-dimethylnonyl propanoate, the female sex pheromone of the western corn rootworm (Diabrotica virgifera virgifera LeConte), was synthesized in four different ways by employing one of the following four reactions as the key step: (i) cross metathesis using the Grubbs I catalyst, (ii) cross metathesis using the Grubbs II catalyst, (iii) alkylation of an al...
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