Abstract
A simple and efficient asymmetrical synthesis was performed of a convenient bifunctional building block, methyl (R)-5,5-dimethoxy-3-methylpentanoate and its (S)-enantiomer. The possibility was shown of its application to the synthesis of insect pheromones.
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Yakovleva, M.P., Khasanova, E.F., Talipov, R.F., and Ishmuratov, G.Yu., Vestn. Bashk. Unst., 2009, vol. 14, p. 1072.
Mori, K. Tetrahedron, 1989, vol. 45, p. 3233.
Ishmuratov, G.Yu., Kharisov, R.Ya., Odinokov, V.N., and Tolstikov, G.A. Usp. Khim., 1994, vol. 63, p. 580.
Mori, K. and Kuwahara, S., Tetrahedron, 1982, vol. 38, p. 521.
Kharisov, R.Ya., Botsman, O.V., Gazetdinov, R.R., Ishmuratov, G.Yu., and Tolstikov, G.A. Russ. Chem. Bull., 2001, vol. 50, p. 1117.
Kharisov, R.Ya., Gazetdinov, R.R., Botsman, O.V., Muslukhov, R.R., Ishmuratov, G.Yu., and Tolstikov, G.A., Zh. Org. Khim., 2002, vol. 38, p. 1047.
Mineyeva, I.V. and Kulinkovich, O.G. Tetrahedron, Lett., 2010, vol. 51, p. 1836.
Mineeva, I.V. and Kulinkovix, O.G.., Zh. Org. Khim., 2008, vol. 44, p. 1277.
Periasamy, M., Venkatraman, L., Sivakumar, S., Sampathkumar, N., and Ramanathan, C.R., J. Org. Chem., 1999, vol. 64, p. 7643.
Enev, V.S., Kaehlig, H., and Mulzer, J., J. Am. Chem. Soc., 2001, vol. 123, p. 10764.
Ahmed, A., Hoegenauer, E.K., Enev, V.S., Hanbauer, M., Kaehlig, H., Öhler, E., Mulzer, J. J. Org. Chem., 2003, vol. 68, p. 3036.
Ojika, M., Kigoshi, H., Ishigaki, T., Tsukada, I., Tsuboi, T., Ogawa, T., Yamada, K. J. Am. Chem. Soc., 1994, vol. 116, p. 7441.
Ojika, M., Kigoshi, H., Yoshida, Y., Ishigaki, T., Nisiwaki, M., Tsukada, I., Arakawa, M., Ekimoto, H., and Yamada, K., Tetrahedron, 2007, vol. 63, p. 3138.
Mori, K., Kuwahara, S., and Ueda, H., Tetrahedron, 1983, vol. 39, p. 2439.
Takano, S., Masuda, K., and Ogasawara, K., Heterocycles, 1981, vol. 16, p. 1509.
Williams, D.R., Mi, L., Mullins, R.J., and Stites, R.E., Tetrahedron Lett., 2002, vol. 43, p. 4841.
Wender, P.A., Hegde, S.G., Hubbard, R.D., and Zhong, L., J. Am. Chem. Soc., 2002, vol. 124, p. 4956.
Wender, P.A., Hilinski, M.K., Skaanderup, P.R., Soldermann, N.G., Mooberry, S.L. Org. Lett., 2006, vol. 8, p. 4105.
Poppe, L., Novak, L., Kolonits, P., Bata, A., and Szantay, Tetrahedron Lett., 1986, vol. 27, p. 5769.
Poppe, L., Novak, L., Kolonits, P., Bata, A., and Szantay, C., Tetrahedron., 1988, vol. 44, p. 1477.
Alvarez, E., Cuvigny, T., Herve, du, Penhoad, C., and Julia, M., Tetrahedron, 1988, vol. 44, p. 119.
Liesener, F.P., Jannsen, U., and Kalesse, M., Synthesis, 2006, p. 2590.
Herold, P., Mohr, P., and Tamm, C., Helv. Shim. Acta, 1983, vol. 66, p. 744.
Mohr, P., Tori, M., Grossen, P., Herold, P., and Tamm, C., Helv. Shim. Acta, 1982, vol. 65, p. 1412.
Mori, K., Suguro, T., and Uchida, M., Tetrahedron, 1978, vol. 34, p. 3119.
Mori, K. and Wu, J., Lieb. Ann., 1991, p. 783.
Evans, D.A., Johnson, J.S., and Olhava, E.J., J. Am. Chem. Soc., 2000, vol. 122, p. 1635.
Lam, L.K.P., Hui, R.A.H.F., and Jones, J.B., J. Org. Chem., 1986, vol. 51, p. 2047.
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Original English Text © I.V. Mineeva, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 2, pp. 262–267.
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Mineeva, I.V. (4R,6R)-6-(hydroxymethyl)-4-methyltetrahydro-2H-pyran-2-one in the synthesis of polyfunctional compounds with the methyl-branched carbon skeleton. Russ J Org Chem 49, 253–258 (2013). https://doi.org/10.1134/S1070428013020127
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DOI: https://doi.org/10.1134/S1070428013020127