Convenient synthesis of mosquito oviposition pheromone and a highly fluorinated analog retaining biological activity (original) (raw)
References
Banks, R.E., andTatlow, J.C. 1986. A guide to modem organofluorine chemistry,in R.E. Banks, D.W.A. Sharp, and J.C. Tatlow (eds.). Fluorine. The First Hundred Years (1886–1986). Elsevier Sequoia, Lausanne, pp. 227–284. Google Scholar
Barua, N.C., andSchmidt, R.R. 1986. Stereoselective synthesis of the major component of a mosquito oviposition attractant pheromone from a β-lithiopropionate equivalent.Tetrahedron 42:4471–4474. Google Scholar
Bruno, D.W., andLaurence, B.R. 1979. The influence of the apical droplet of_Culex_ egg rafts on oviposition of_Culex pipiens fatigans_ (Diptera: Culicidae).J. Med. Entomol. 16:300–305. Google Scholar
Fuganti, C.,Grasselli, P., andServi, S. 1982. Synthesis of the two enantiomeric forms of_erythro_-6-acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone.J. Chem. Soc. Chem. Commun. 1285–1286.
Hwang, Y.-S., Mulla, M.S., Chaney, J.D., Lin, G.-Q., andXu, H.-J. 1987. Attractancy and species specificity of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone_J. Chem. Ecol._ 13:245–252. Google Scholar
Jefford, C.W., Jaggi, D., andBoukouvalas, J. 1986. A short, stereodivergent synthesis of the racemic_erythro_ and_threo_ diastereomers of 6-acetoxy-5-hexadecanolide, a mosquito oviposition attractant pheromone.Tetrahedron Lett. 27:4011–4014. Google Scholar
Ko, K.-Y., andEliel, E.L. 1986. Asymmetric synthesis of (5_R_, 6_S_)-6-acetoxy-5-hexadecanolide, the major component of the oviposition attractant pheromone of the mosquito_Culex pipiens fatigans_, and two of its stereoisomers.J. Org. Chem. 51:5353–5362. Google Scholar
Laurence, B.R., andPickett, J.A. 1982._erythro_-6-Acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone.J. Chem. Soc. Chem. Commun. 59–60.
Laurence, B.R., andPickett, J.A. 1985. An oviposition attractant pheromone in_Culex quinquefasciatus_ Say (Diptera: Culicidae).Bull. Entomol. Res. 75:283–290. Google Scholar
Laurence, B.R., Mori, K., Otsuka, T., Pickett, J.A., andWadhams, L.J. 1985. Absolute configuration of the mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide.J. Chem. Ecol. 11:643–648. Google Scholar
Lin, G.-Q., Xu, H.-J., Wu, B.-C., Guo, G.-Z., andZhou, W.-S. 1985. Studies on the identification and synthesis of insect pheromones. XXI. Stereoselective synthesis of all the possible optical isomers of the mosquito oviposition attractant pheromone.Tetrahedron Lett. 26:1233–1236. Google Scholar
Machiya, K., Ichimoto, I., Kirihata, M., andUeda, H. 1985. A convenient synthesis of four stereoisomers of 6-acetoxy-5-hexadecanolide, the major component of the mosquito oviposition attractant pheromone.Agric. Biol. Chem. 49:643–649. Google Scholar
Mori, K., andOtsuka, T. 1983. Synthesis of both the enantiomers of_erythro_-6-acetoxy-5-hexadecanolide.Tetrahedron 39:3267–3269. Google Scholar
Mukaiyama, T., Banno, K., andNarasaka, K. 1974. New cross-aldol reactions. Reactions of silyl enol ethers with carbonyl compounds activated by titanium tetrachloride.J. Am. Chem. Soc. 96:7503–7509. Google Scholar
Ochiai, M.,Ukita, T.,Nagao, Y., andFujita, E. 1985. Stereochemistry of an oxidative 1,4-fragmentation of γ-stannyl alcohols with a hypervalent organoiodine compound and the synthesis of_erythro_-6-acetoxyhexadecan-5-olide.J. Chem. Soc. Chem. Commun. 637–638.
Otieno, W.A., Onyango, T.O., Pile, M.M., Laurence, B.R., Dawson, G.W., Wadhams, L.J., andPickett, J.A. 1988. A field trial of the synthetic oviposition pheromone with_Culex quinquefasciatus_ Say (Diptera: Culicidae) in Kenya.Bull. Entomol. Res. 78:463–470. Google Scholar
Prestwich, G. D., Wei-Chuan, Sun, Mayer, M. S., andDickens, J. C. 1990. Perfluorinated mothpheromones: Synthesis and electrophysiological activity.J. Chem. Ecol. 16:1761–1778. Google Scholar
Sato, T.,Watanabe, M.,Honda, N., andFujisawa, T. 1984. Synthesis of both enantiomers of_erythro_-6-acetoxy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone.Chem. Lett. 1175–1176.
Wang, Z-M., Qian, X-H., andZhou, W-S. 1990. Stereoselective synthesis of (−)-(5_R_,6_S_)-6-acetoxy-5-hexadecanolide, the mosquito oviposition attractant pheromone.Tetrahedron 46:1191–1198. Google Scholar