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Compound - trans-eldanolide
 


Bedoukain

 
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(E)-3,7-Dimethyl-6-octene-4-olide
(E)-3,7-Dimethyl-6-octene-4-olide

Formula: C10H16O2 
CAS#: 81469-34-3 
MW: 168.23 

[MS]  [ NMR ]  [Behavioural function]  [Chemdraw





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Reference(s) for synthesis of (E)-3,7-Dimethyl-6-octene-4-olide



Barua, N.C., and Schmidt, R.R. 1986. ß-Lithioacrylate equivalents for the synthesis of (±)-eldanolide. Synthesis. 11:891-893.
 
Burger, B.V., Nell, A.E., Smit, D., Spies, H.S.C., Mackenroth, W.M., Groche, D., and Atkinson, P.R. 1993. Constituents of wing gland and abdominal hair pencil secretions of male African sugarcane borer, Eldana saccarina Walker (Lepidoptera: Pyralidae). J. Chem. Ecol. 19:2255-2277.
 
Butt, S., Geoff Davies, H., Dawson, M.J., Lawrence, G.C., Leaver, J., Roberts, S.M., Turner, M.K., Wakefield, B.J., Wall, W.F., and Winders, J.A. 1987. Resolution of 7,7-dimethylbicyclo[3.2.0]hept-2-en-6-one using Mortierella ramanniana and 3alpha, 20ß-hydroxy-steroid dehydrogenase, photochemistry of 3-hydroxy-7,7dimethylbicyclo[3 2.0]heptan-6-ones, and the synthesis of (+)-eldanolide. J. Chem. Soc. Perkin Trans. 1:903-907.
 
Chakraborty, T.K., and Chandrasekaran, S. 1984. Efficient transformation of ()-2-butene-1,4-diols to ,-butenolides: a simple synthesis of (±)-eldanolide. Tetrahedron Lett. 25:2891-2894.
 
Dziadulewicz, E., and Gallagher, T. 1985. ß-substituted ketene thioacetals as ß-lithioacrylate equivalents. The synthesis of (±)-eldanolide. Tetrahedron Lett. 26:4547-4550. .
 
Frauenrath, H., and Philipps, T. 1985. Diastereoselektive synthese von cis- oder trans-2,3-substituierten tetrahydrofuranen und 3,4-substituierten 4-butanoliden. Liebigs Ann. Chem. 1951.
 
Frauenrath, H., and Philipps, T. 1986. A simple diastereoselective synthesis of (±)-eldanolide. Tetrahedron. 42:1135-1138.
 
Hizuka, M., Hayashi, N., Kamashita, T., Suemune, H., and Sakai, K. 1988. Chem. Pharm. Bull. 36:1550-1553.
 
Iriye, R. 1985. Transformation of 3,7-dimethyl-2,6-octadienal (citral) into racemic eldanolide (wing gland pheromone of the male African sugar-cane borer; Eldana saccharina) (Wlk.). Agric. Biol. Chem. 49:2775.
 
Jefford, C.W., Sledeski, A.W., Boukouvalas, J. 1987. A direct synthesis of (±)-eldanolide via the highly regioselective prenylation of 2-trimethylsiloxyfuran. Tetrahedron Lett. 28:949-950.
 
Kunesch, G., Zagatti, P., Lallemand, J.Y., Debal, A., and Vigneron, J.P. 1981. Structure and synthesis of the wing gland pheromone of the male African sugar-cane borer: Eldana saccharina (Wlk.). Tetrahedron Lett. 22:5270-5274.
 
Kunesch, G., Zagatti, P., Lallemand, J.Y., Larcheveque, M., Debal, A., and Francke, W. 1981. Male sex pheromones of the African sugarcane borer: Eldana saccharina Wlk.: identification and synthesis. Coll. INRA. 7:281.
 
Matteson, D.S., Sadhu, K.M., and Peterson, M.C. 1986. 99% Chirally-selective syntheses via Pinandiol boronic esters: insect pheromones, diols, and an amino acid. J. Am. Chem. Soc. 108:810-819.
 
Ortuno, R.M., Merce, R., and Font, J. 1986. Total synthesis of (+)-eldanolide from D-ribonolactone. Tetrahedron Lett. 27:2519-2522.
 
Suzuki, K., Ohkuma, T., and Tsuchihashi, G.-I. 1985. Enantio- and diastereo-controlled synthesis of (+)- and (-)-eldanolide based on asymmetric pinacol-type rearrangement. Tetrahedron Lett. 26:861-864.
 
Uematsu, T., Umemura, T., and Mori, K. 1983. Synthesis of both the enantiomers of eldanolide (trans-3,7-dimethyl-6-octen-4-olide), the wing gland pheromone of the male African sugar-cane borer. Agric. Biol. Chem. 47:597.
 
Vigneron, J.P., Meric, R., Larcheveque, M., Debal, A., Kunesch, G., Zagatti, P., and Gallois, M. 1982. Absolute configuration of eldanolide, the wing gland pheromone of the male African sugar cane borer. Eldana saccharina (Wlk.). Synthesis of its (+) and (-) enantiomers. Tetrahedron Lett. 23:5051-5054.
 
Vigneron, J.P., Meric, R., Larcheveque, M., Debal, A., Lallemand, J.Y., Kunesch, G., Zagatti, P., and Gallois, M. 1984. L 'eldanolide, pheromone des glandes alaires de la pyrale de la canne a sucre, Eldana saccharalis (Wlk ): structure et synthese de ses deux enantiomeres. Tetrahedron. 40:3521-3529.
 
Vigneron, J.P., Meric, R., Larcheveque, M., Debal, A., Lallemand, J.Y., Kunesch, G., Zagatti, P., and Gallois, M. 1984. L'eldanolide, phéromone des glandes alaires de la pyrale de la canne à sucre, eldana saccharina (Wlk.): structure et synthèse de ses deux énantiomères. Tetrahedron. 40:3521-3530.
 
Whittaker, M. 1986. Asymmetric synthesis towards eldanolide: pheromone of the African sugar cane borer. Chem. Ind. (London). 463.
 
Yokoyama, Y., and Yunokihara, M. 1983. Chirality transfer during cyclobutyl-cyclopropyl methyl-homoallyl cation rearrangement and synthesis of (-)-eldanolide. Chem. Lett. 1245.
 

 
Citation: El-Sayed AM 2014. The Pherobase: Database of Insect Pheromones and Semiochemicals. <http://www.pherobase.com>.
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