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Compound - R-japonilure [(R)-(Z)-5-(Dec-1-enyl)-oxacyclopentan-2-one]

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(R)-(Z)-5-(Dec-1-enyl)-oxacyclopentan-2-one Formula:  C14H24O2  CAS#:    MW:  224.34  [MS]  [ NMR ]  [Behavioural function]

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Reference(s) for synthesis of (R)-(Z)-5-(Dec-1-enyl)-oxacyclopentan-2-one [R-japonilure] Baker, R., and Rao, V.B. 1982. Synthesis of optically pure (R,Z)-5-dec-1-enyloxacyclopentan-2-one, the sex pheromone of the Japanese beetle. J. Chem. Soc. Perkin Trans. 1:69-71.   Bernard, A.M., Frongia, A., Piras, P.P., and Secci, F. 2003. Unexpected stereochemistry in the lithium stalt catalyzed ring expansion of nonracemic oxaspiropentanes. Formal syntheses of (-)-(4R,5R)-muricatacin and the pheromone (R)-japonilure. Org. Lett. 5:2923-2926.   Doolittle, R.E., Tumlinson, J.H., Proveaux, A.T., and Heath, R.R. 1980. Synthesis of the sex pheromone of the Japanese beetle. J. Chem. Ecol. 6:473-485.   Dos Santosa, A.A., and Francke, W. 2006. Convergent and enantioselective syntheses of both enantiomers of (5Z)-tetradecen-4-olide, scarab beetle pheromones. Tetrahedron: Asymmetry. 17:2487-2490.   Hiscox, W.C., and Matteson, D.S. 2000. Asymmetric synthesis of the Japanese beetle pheromone via boronic esters. J. Organomet. Chem. 614-615:314-317.   Midland, M.M., and Nguyen, N.H. 1981. Asymmetric synthesis of gamma-lactones. A facile synthesis of the sex pheromone of the Japanese beetle. J. Org. Chem. 46:4107-4108.   Nishida, Y., Konno, M., Hori, H., Ohrui, H., and Meguro, H. 1986. Application of the benzoate chirality method for t-lactones with unsaturation at the C5 position via acyclic allylic alcohols, and confirmation of the absolute configurations of Japanese beetle's sex pheromone and Marmelo lactones. Agric. Biol. Chem. 50:187.   Nishizawa, M., Yamada, M., and Noyori, R. 1981. Highly enantioselective reduction of alkynyl ketones by a binaphtholmodified aluminum hydride reagent. Asymmetric synthesis of some insect pheromones. Tetrahedron Lett. 22:247-250.   Noyori, R., Tomino, I., Yamada, M., and Nishizawa, M. 1984. Synthetic applications of the enantioselective reduction by binaphthol-modified lithium aluminum hydride reagents. J. Am. Chem. Soc. 106:6717.   Pirkle, W.H., and Adams, P.E. 1979. Broad-spectrum synthesis of enantiomerically pure lactones. I. Synthesis of sex pheromones of the carpenter bee, rove beetle, Japanese beetle, black-tailed deer, and oriental Hornet. J. Org. Chem. 44:2169-2175.   Sato, K., Nakayama, T., and Mori, K. 1979. New synthesis of both enantiomers of (Z)-5-(1-decenyl)-oxacyclopentan-2-one, the pheromone of the Japanese beetle. Agric. Biol. Chem. 43:1571.   Senda, S., and Mori, K. 1983. Asymmetric synthesis of (R,Z)-(-)-5-(1-decenyl)oxacyclopentan-2-one, the pheromone of the Japanese beetle. Agric. Biol. Chem. 47:2595.   Tumlinson, J.H., Klein, M.G., Doolittle, R.E., Ladd, T.L., and Proveaux, A.T. 1977. Identification of the female Japanese beetle sex pheromone: inhibition of male response by an enantiomer. Science. 197:789.