Abstract
A simple stereospecific synthesis of (Z,Z)-3,5-tetradecadienoic acid is described based upon coupling of 1-decyne and 3-butyn-1-ol to give 3,5-tetradecadiyn-1-ol. Subsequent reduction of the diyne to (Z,Z)-3,5-tetradecadien-1-ol and oxidation of the dienol gave the desired acid.Attagenus elongatulus were strongly attracted to the pure acid.
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References
Brandsma, L. 1971. Preparative Acetylene Chemistry. American Elsevier, New York, p. 98 (1-bromo alkyne), p. 169 (Chodkiewitz).
Brown, H.C., Garg, C.P., andLiu, K.-T. 1971. The oxidation of secondary alcohols in diethyl ether with aqueous chromic acid. A convenient procedure for the preparation of ketones in high epimeric purity.J. Org. Chem. 31:387–390.
Corey, E.J., andSchmidt, G. 1979. Useful procedures for the oxidation of alcohols involving pyridinium dichromate in aprotic media.Tetrahedron Lett. 5:399–402.
Craig, J.C., andHorning, E.C. 1960. Preparation of esters by hemiacetal oxidation.J. Org. Chem. 25:2098–2102.
Djerassi, C., Engle, R.R., andBowers, A. 1956. The direct conversion of steroidai Δ5-3β-alcohols to Δ5 and Δ4-3-ketones.J. Org. Chem. 21:1547–1549.
Fieser, L.F., andFieser, M. 1967. Reagents for Organic Synthesis, Vol. 1. John Wiley & Sons, New York, p. 142.
Fukui, H., Matsumura, F., Barak, A.V., andBurkholder, W.E. 1977. Isolation and identification of a major sex-attracting component ofAttagenus elongatulus (Casey) (Coleoptera: Dermestidae).J. Chem. Ecol. 3:539–548.
Holland, B.C., andGilman, N.W. 1974. An improved procedure for the oxidation of alkynols to alkynoic acids.Synth. Commun. 4:203–210.
Landini, D.,Montanari, F., andRolla, F. 1979. Selective oxidation of primary alcohols to aldehydes under phase-transfer conditions.Synthesis 134–136.
Lindlar, H., andDubuis, R. 1966. Palladium catalyst for partial reduction of acetylenes.Org. Synth. 46:89–92.
Pletcher, D., andTait, S J.D. 1978. A procedure for the oxidation of alcohols of aldehydes based on phase transfer catalysts.Tetrahedron Lett. 19:1601–1602.
Rodin, J.O., Leaffer, M.A., andSilverstein, R.M. 1970. Synthesis oftrans-3,itcis-5-tetradeca-dienoic acid (megatomoic acid), the sex attractant of the black carpet beetle, and its geometric isomers.J. Org. Chem. 35:3152–3154.
Silverstein, R.M., Rodin, J.O., Burkholder, W.E., andGorman, J.E. 1967. Sex attractant of the black carpet beetle.Science 157:85–87.
Svirskaya, P.I., Leznoff, C.C., andRoelofs, W.L. 1980. A steroselective synthesis of acis,cis conjugated dienol, A candidate pheromone.Synth. Commun. 10:391–397.
Valicenti, A.J., andHolman, R.T. 1976. Oxidation of long-chain alcohols to aldehydes by the dipyridine chromic anhydride complex.Chem. Phys. Lipids 17:389–392.
Zweifel, G., andPolston, N.L. 1970. Selective hydroboration of conjugated diynes with dialkylboranes. A convenient route to conjugatedcis-enynes, α,β-acetylenic ketones, andcis,cis- dienes.J. Am. Chem. Soc. 92:4068–4071.
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De Jarlais, W.J., Emken, E.A. Stereospecific synthesis of (Z,Z)-3,5-tetradecadienoic acid, a component ofAttagenus elongatulus (Casey) pheromone. J Chem Ecol 13, 179–184 (1987). https://doi.org/10.1007/BF01020361
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DOI: https://doi.org/10.1007/BF01020361