Reference(s) for synthesis of (Z)-6-Heneicosen-11-one [Z6-21-11Kt]
| Akermark, B., and Ljungqvist, A. 1978. Eutectic potassium-sodium-aluminum chloride as a mild catalyst for ene reactions: simple synthesis of the sex pheromone from Douglas fir tussock moth. J. Org. Chem. 43:4387-4388. |
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| Bestmann, H.J., and Schmidt, M. 1985. Pheromone 51. Synthese von ungesaettigten pheromonketonen aus Orgyia pseudotsugata (Douglas fir tussock moth) und Carposina niponensis (peach fruit moth). Tetrahedron Lett. 26:6171-6174. |
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| Cahiez, G., Alexakis, A., and Normant, J.F. 1980. Simple stereospecific synthesis of the insect sex pheromones of Cossus cossus, Eupoecilia ambiguella, and Orgyia pseudotsugata. Tetrahedron Lett. 21:1433-1436. |
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| Fernandez, S., Quintanilla, R., and Hernandez, J.E. 1983. Reductive cleavage of 2-acyl tetrahydrofuranes. Synthesis of (Z)-6-heneicosen-11-one, pheromone of the Douglas fir tussock moth. Synth. Comm. 13:621. |
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| Fetizon, M., and Lazare, C. 1978. A rapid and convenient synthesis of tbe sex pheromone of the Douglas fir, Lepidoptera Orgyia pseudotsugata. J. Chem. Soc. Perkin Trans. 1:842-844. |
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| Henrick, C.A. 1977. The synthesis of insect sex pheromones. Tetrahedron. 33:1845-1889. |
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| Hernandez, J.E., Cisneros, A., and Fernandez, S. 1983. Short syntheses of unsaturated aliphatic ketone pheromones. Synth. Comm. 13:191. |
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| Kocienski, P.J., and Cernigliaro, G.J. 1976. A synthesis of (Z)-6-heneicosen-11-one. The sex pheromone of the Douglas fir tussock moth. J. Org. Chem. 41:2927-2928. |
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| Kondo, K., and Muraitashi, S.-I. 1979. Selective transformation of organoboranes to Grignard reagents by using pentane-1,5-di(Magnesium bromide). Syntheses of the pheromones of Southern armyworm moth and Douglas fir tussock moth. Tetrahedron Lett. 20:1237-1240. |
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| Larson, G.L., Hernandez, D., de Lopez-Cepero, I.M., and Torres, L.E. 1985. Reaction of alpha-silyl esters with Grignard reagents: a synthesis of ß-keto silanes and ketones. Preparation of the Douglas fir tussock moth pheromone. J. Org. Chem. 50:5260-5267. |
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| Mori, K., Uchida, M., and Matsui, M. 1977. Synthesis of aliphatic insect pheromones from alicyclic starting materials. (Z)-6-heneicosen-11-one and (Z)-8-dodecenyl acetate. Tetrahedron. 33:385-387. |
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| Mundy, B.P., and Bjorklund, M. 1985. Novel synthesis of the sex pheromone of the Douglas-fir tussock moth (Orgyia pseudotsugata) and solenopsin A, a constituent of fire ant venom. Tetrahedron Lett. 26:3899-3902. |
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| Murata, Y, Inomata, K., Kinoshita, H., and Kotake, H. 1983. A convenient method for the synthesis of acyclic ketones. Synthesis of sex pheromone of Douglas fir tussock moth. Bull. Chem. Soc. Jpn. 56:2539. |
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| Muto, S.-E., and Mori, K. 2003. Synthesis of the four components of the female sex pheromone painted apple moth, Teia anartoides. Biosci. Biotechn. Biochem. 67:1559-1567. |
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| Naoshima, Y., Ike, H., Ogawa, T., Nakayama, T., and Kondo, H. 1984. An easy synthesis of (E)-9-oxo-2-decenoic acid, the queen substance of the honey bee, and (Z)-6-heneicosen-11-one, the sex pheromone of the Douglas fir tussock moth. Agric. Biol. Chem. 48:2151. |
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| Nishiyama, H., Sakuta, K., and Itoh, K. 1984. New stereocontrolled approach to some insect pheromones via silicon-directed Beckmann fragmentations. Tetrahedron Lett. 25:223-226. |
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| Ousset, J.B., Mioskowski, C., Yang, Y.-L., and Falck, J.R. 1984. Enol ethers: preparation and synthetic applications. Tetrahedron Lett. 25:5903-5906. |
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| Pramod, K., Ramanathan, H., and Subba Rao, G.S.R. 1983. Strategic synthesis based on cyclohexadienes: preparation of 2-, 2,3- and 2,4-substituted cyclohexenones: synthesis of (Z)-heneicosa-6-en-11-one. J. Chem. Soc. Perkin Trans. 1:7-10. |
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| Reddy, G.B., and Mitra, R.B. 1986. Acetone dimethyl hydrazone: useful synthon for the synthesis of pheromones with keto and spiro ketal functions. Synth. Comm. 16:1723. |
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| Reddy, G.B., and Mitra, R.B. 1987. A simple and short synthesis of Z-6-heneicosen-11-one and Z-1,6-heneicosen-11-one, the sex pheromones of Douglas-fir tussock moth. Synth. Comm. 17:893. |
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| Reddy, P.S., Sahasrabudhe, A.B., and Yadav, J.S. 1983. A convenient synthesis of (Z)-6-heneicosen-11-one - a sex pheromone of the Douglas-fir tussock moth. Synth. Comm. 13:379. |
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| Schäfer, H.J. 1979. Recent synthetic applications of kolbe electrolysis. Chem. Phys. Lipids. 24:321-333. |
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| Scholz, D. 1984. Ketosulfone als ethylencarbanionenaequivalente: die synthese von 6-nonen-1-ol, 7-dodecen-1-ol-acetat und 6-heneicosen-11-on, drei Insektenpheromonen. Sci. Pharm. 52:151. |
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| Smith, L.M., Smith, R.G., Loehr, T.M., Daves, G.D., Jr., Daterman, G,E., and Wohler, R.H. 1978. Douglas fir tussock moth pheromone: identification of a diene analogue of the principal attractant and synthesis of stereochemically defined 1,6-, 2,6-, and 3,6-heneicosadien-11-ones. J. Org. Chem. 43:2361-2366. |
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| Smith, R.G., Daterman, G.E., and Daves, G.D., Jr. 1975. Douglas fir tussock moth: sex pheromone identification and synthesis. Science. 188:63-64. |
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| Smith, R.G., Daves, G.D., Jr., and Daterman, G.E. 1975. Synthesis of (Z)-6-heneicosen-11-one. Douglas fir tussock moth sex attractant. J. Org. Chem. 40:1593-1595. |
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| Sokolovskaya, S.V. 1980. Simple synthesis of (Z)-6-heneicosen-11-one - sex pheromone of Orgyia pseudotsugata. Khim. Prir. Soedin. 102. |
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| Sonnet, P.E. 1983. Improved preparations of alkyne nitriles, acetates, and alcohols. Application to the synthesis of the sex pheromone components of the Douglas fir tussock moth and peach fruit moth. J. Chem. Ecol. 9:551-560. |
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| Trost, B.M., and Ornstein, P.L. 1981. A chemoselective desulfurization method via homogeneous Nickel catalysis. Tetrahedron Lett. 22:3463-3466. |
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| Vig, O.P., Sharma, M.L., Verma, N.K., and Malik, N. 1980. A new synthesis of (Z)-heneicos-6-en-11-one, sex pheromone of Douglas fir, Lepidoptera Orgyia pseudotsugata. Ind. J. Chem. B. 19:950. |
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| Wang, K.K., and Chu, K.-H. 1984. Preparation of (Z)-alkenes, ketones, and alkynes via trialkyltin chloride induced intramolecular transfer reaction of Lithium 1-alkynyltrialkylborates. Stereoselective synthesis of the sex pheromones of the Douglas fir tussock moth, the gypsy moth, and the wild silkmoth Antheraea polyphemus. J. Org. Chem. 49:5175-5178. |
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| Wenkert, E., Ferreira, V.F., Michelotti, E.L., and Tingoli, M. 1985. Synthesis of acyclic, cis olefinic pheromones by way of Nickel-catalyzed Grignard reactions. J. Org. Chem. 50:719-721. |
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| Williams, H.J., Jr. 1977. I. Preparation of pheromones through cleavage reactions of ß-halo-alpha,ß-unsaturated ketones. II. Preparation of pheromones and pheromone analogues using other methods. III. Preparation of optically active alpha-methylene-gamma-lactones, Ph. D. thesis, University of North Carolina, Raleigh, NC. |
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