Abstract
A 2% cross-linked styrene-divinylbenzene copolymer containing pendant trityl chloride groups was used as the solid support in the synthesis of (Z, Z)-3,13-octadecadien-1-yl acetate, a component of the sex attractant of the lesser peachtree borer,Synanthedon pictipes, the peachtree borer,Synanthedon exitiosa, and the cherry tree borer,Synanthedon hector. This solid-phase synthesis is compared with a similar synthetic approach in solution. The solid-phase synthesis of (Z, Z)-7,11-hexadecadien-1-yl acetate, a component of the pheromone of the pink bollworm moth,Pectinophora gossypiella is described.
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Alvarado-Urbina, G., Sathe, G.M., Liu, W.C., Cillen, M.F., Duck, P.D., Bender, R., andOgilvie, K.K. 1981. Automated synthesis of gene fragments.Science 214:270–274.
Ames, D.E., andGoodburn, T.G. 1967. Synthesis of long-chain acid. Part VIII. 9,10,18-Trihydroxyoctadecanoic Acid.J. Chem. Soc. (C) 1556–1558.
Anderson, R.J., andHenrick, C.A. 1975. Stereochemical control in Wittig olefin synthesis. Preparation of the pink bollworm sex pheromone mixture, gossyplure.J. Am. Chem. Soc. 97:4327–4333.
Anzilotti, W.F., andVogt, R.R. 1939. The preparation of α-Alkylβ-alkenylacetylenes.J. Am. Chem. Soc. 61:572–573.
Brown, H.C., andZweifel, G. 1961. Hydroboration XI. The hyroboration of acetylenes—a convenient conversion of internal acetylenes intocis-olefins and the terminal acetylenes into aldehydes.J. Am. Chem. Soc. 83:3834–3840.
Burgstahler, A.W., Weigel, L.O., Sanders, M.E., Shaefer, C.G., Bell, W.J., andVuturo, S.B. 1977. Synthesis and activity of 29-hydroxy-3, 11-dimethyl-2-nonacosanone, Component B of the german cockroach sex pheromones.J. Org. Chem. 42:566–568.
Disselnkötter, H., Eiter, K., Kare, W., andWendish, W. 1976. Trennung und analytische Bestimmung synthetischer Pheromone am Beispiel der isomeren 7,11-Hexadecadien-1-ylacetate (Gossyplure)Tetrahedron 32:1591–1595.
Doolittle, R.E., Proveaux, A.T., andHeath, R.R. 1980. Synthesis of sex pheromones of lesser peachtree borer.J. Chem. Ecol. 6(1):271–83.
Ebata, T., andMori, K. 1979. A convenient synthesis of a mixture of (Z, Z)-3,13-octadecadienyl acetate and its (E, Z) isomer, the attractant for the cherrytree borer.Agric. Biol. Chem. 43:1567–1570.
Erickson, B.W., andMerrifield, R.B. 1976, pp. 255–527. In H. Neurath and R.L. Hill (eds.). The Proteins. 3rd ed., Vol. II, Academic Press, New York.
Fréchet, J.M.J. 1981. Synthesis and applications of organic polymers as supports and protecting groups.Tetrahedron 37:663–683.
FrÉchet, J.M.J., andNuyens, L.J. 1976. Use of polymers as protecting groups in organic synthesis. III. Selective functionalization of polyhydroxyalcohols.Can. J. Chem. 54: 926–934.
Fyles, T.M., andLeznoff, C.C. 1976. The use of polymer supports in organic synthesis. V. The preparation of monoacetates of symmetrical diols.Can. J. Chem. 54:935–942.
Fyles, T. M., Leznoff, C.C., andWeatherston, J. 1977. The use of polymer supports in organic synthesis. XII. The total stereoselective synthesis of cis insect sex attractants on solid phases.Can. J. Chem. 55:4135–4143.
Henrick, C.A. 1977. The synthesis of insect sex pheromones.Tetrahedron 33:1845–1889.
Jones, A.J., Leznoff, C.C., andSvirskaya, P.I. 1982. Characterization of organic substrates bound to crosslinked polystyrenes by13C NMR spectroscopy.Org. Magn. Reson. 18:236–240.
Leznoff, C.C., Fyles, T.M., andWeatherston, J. 1977. The use of polymer supports in organic synthesis. VIII. Solid phase syntheses of insect sex attractants.Can. J. Chem. 55:1143–1153.
Leznoff, C.C. 1978. The use of insoluble polymer supports in general organic synthesis.Acc. Chem. Res. 11:327–333.
Mori, K., Tominaga, M., andMatsui, M. 1975. Stereoselective synthesis of the pink bollworm sex pheromone, (Z, Z)-7, 11-hexadecadienyl acetate and its (Z,Z) isomer.Tetrahedron 31:1846–1848.
Rossi, R., 1977. Insect pheromones; 1 Synthesis of achiral components of insect pheromones.Synthesis 13:817–836.
Schwartz, M., andWaters, R.M. 1972. Insect sex attractants; XII. An efficient procedure for the preparation of unsaturated alcohols and acetates.Synthesis 8:567–568.
Still, C.W., Kahn, M., andMitra, A. 1978. Rapid Chromatographie technique for preparative separations with moderate resolution.J. Org. Chem. 43(14):2923–2925.
Su, H.C.F., andMahany, G. 1974. Synthesis of the sex pheromone of the female Angoumois grain moth and its geometric isomers.J. Econ. Entomol. 67:319.
Svirskaya, P.I., Leznoff, C.C., Weatherston, J., andLaing, J.E. 1979. Synthesis oftrans-alken-1-ols as candidates for insect sex attractants.J. Chem. Eng. Data 24:152–155.
Svirskaya, P., Leznoff, C.C., andRoelofs, W.L. 1980. A steroselective synthesis of acis,cis conjugated dienol, a candidate pheromone.Synth. Commun. 10(5):391–397.
Uchida, M., Mori, K., andMatsui, M. 1978. Synthesis of (Z, Z)-3,13-octadecadienylacetate and its (E,Z) isomer, the attractant for the cherrytree borer.Agric. Biol. Chem. 42(5): 1067–1070.
Zweifel, G., andPolston, N.L. 1970. Selective hydroboration of conjugated diynes with dialkylborane. A convenient route to conjugatedcis-enynes α,β-acetylenic ketones, andcis, cis-dienes.J. Am. Chem. Soc. 92:4068–4071.
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Svirskaya, P.I., Leznoff, C.C. Syntheses of unconjugated (Z,Z)-diolefinic insect pheromones on insoluble polymer supports. J Chem Ecol 10, 321–333 (1984). https://doi.org/10.1007/BF00987860
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DOI: https://doi.org/10.1007/BF00987860