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A Convenient Preparation Of Ambergris Odorants From Copalic Acid
Registro en:
Journal Of The Brazilian Chemical Society. , v. 7, n. 3, p. 181 - 186, 1996.
1035053
2-s2.0-0001277763
Autor
Nunes F.M.N.
Imamura P.M.
Institución
Resumen
The syntheses of the ambergris odorants ent-epi-8-ambraketal (7), ent-ambrox (10), and two oxides 13 and 14 starting from copalic acid (2a) are described. 7 3 181 186 Ohloff, G., (1982) Fragrance Chemistry, pp. 535-545. , Theimer, E.T., Ed. Academic Press: New York Stoll, M., Hinder, M., (1950) Helv. Chim. Acta, 33, p. 1251 Helv. Chim. Acta, p. 1308 Sell, C., (1990) Chem. & Ind., 20, p. 516 Barton, D.H.R., Parekh, S.I., Taylor, D.K., Tse, C., (1994) Tetrahedron Lett., 35, p. 5801 Costa, M.C., Tavares, R., Motherwell, W.B., Curto, M.J.M., (1994) Tetrahedron Lett., 35, p. 8839 Barrero, A.F., Sánchez, J.F., Manzaneda, E.J.A., Altarejoss, J., Muñoz, M., Haidour, A., (1994) Tetrahedron, 50, p. 6653. , and the references cited therein Wolf, H., Mätzel, U., Brunke, E.J., Klein, E., (1979) Tetrahedron Lett., 25, p. 2339 Kawanobe, T., Kogami, K., Matsui, M., (1986) Agric. Biol. Chem., 50, p. 1475 Buchi, G., Wüest, H., (1989) Helv. Chim. Acta, 72, p. 996 Snowden, R.L., Linder, S.M., (1991) Tetrahedron Lett., 32, p. 4119 Snowden, R.L., Eichenbergher, J.C., Linder, S.M., Sonnay, P., Vial, C., Schulte-Elte, K.H., (1992) J. Org. Chem., 57, p. 955 Barco, A., Benetti, S., Bianchi, A., Casolari, A., Guarneri, M., Pollini, G.P., (1995) Tetrahedron, 51, p. 8333 Mori, K., Tamura, T., (1990) Liebigs Ann. Chim., p. 361 Paquette, L.A., Maleczka Jr., R.E., (1991) J. Org. Chem., 56, p. 912 Verstegen-Haaksa, A.A., Smarts, H.J., Jansen, B.J.M., De Groot, A., (1994) Tetrahedron, 50, p. 10095 Sierra, M.G., Rúveda, E.A., López, J.T., Cortés, M.J., (1987) Heterocycles, 26, p. 2801 Maturana, H., López, J.T., Cortés, M.J., (1991) Synth. Commun., 21, p. 1533 Nishi, Y., Ishihara, H., (1989) J. Jpn. Oil Chem. Soc., 38, p. 276 Urones, J.G., Bisaber, P., Marcos, I.S., González, J.L., Jiménez, V., Sexmero, M.J., Lithgow, A.M., (1992) Tetrahedron, 48, p. 9991 Koyama, H., Kaku, Y., Ohno, M., (1987) Tetrahedron Lett., 28, p. 2863 Buchbauer, G., Heines, V.M., Krejei, V., Talsky, C., Wunderer, H., (1985) Monat. fur Chem., 116, p. 1345 Cambie, R.C., Franich, R.A., Larsen, D., Rutledge, P.S., Ryan, G.R., Woodgate, P.D., (1990) Aust. J. Chem., 43, p. 21 Barrero, A.F., Altarejos, J., Manzaneda, E.J.A., Ramos, J.M., Salido, S., (1993) Tetrahedron, 49, p. 9525 Tetrahedron, p. 6251 Schenk, H.R., Gutman, H., Jeger, O., Ruzicka, L., (1954) Helv. Chim. Acta, 26, p. 2801 Cambie, R.C., Joblin, K.N., Preston, A.F., (1971) Austr. J. Chem., 24, p. 583 Martres, P., Perfetti, P., Zahra, J.-P., Waegell, B., (1994) Tetrahedron Lett., 35, p. 5801 Barrero, A.F., Manzaneda, E.J.A., Altarejos, J., Salido, S., Ramos, J.M., (1993) Tetrahedron, 49, p. 10405 Martres, P., Perfetti, P., Zahra, J.-P., Waegell, B., Giraudi, E., Petrzilka, M., (1993) Tetrahedron Lett., 34, p. 8081. , and the references cited therein Imamura, P.M., Rúveda, E.A., (1980) J. Org. Chem., 45, p. 510 Nunes, D.S., Brendolan, G., Imamura, P.M., Sierra, M.G., Marsaioli, A.J., Rúveda, E.A., (1981) J. Org. Chem., 46, p. 4851 Imamura, P.M., Pantarotto, H., (1995) Liebigs Ann. Chim., p. 1891 noteDemole, E., Wüest, H., (1967) Helv. Chim. Acta, 50, p. 1314 notenoteOhloff, G., Giersch, W., Pickenhagen, W., Furrer, A., Frei, B., (1985) Helv. Chim. Acta, 68, p. 2022 noteDey, A.K., Wolf, H.R., (1978) Helv. Chim. Acta, 61, p. 1004 Ohloff, G., Vial, C., Wolf, H.R., Job, K., Jégou, E., Polonsky, J., Ledere, E., (1980) Helv. Chim. Acta, 63, p. 1932 Dimoglo, A.S., Vlad, P.F., Shvets, N.M., Coltsa, M.N., Güzel, Y., Saraçoglu, M., Saripinar, E., Patat, S., (1995) New J. Chem., 19, p. 1217 Scheidegger, U., Schaffner, K., Jeger, O., (1962) Helv. Chim. Acta, 45, p. 400 Ohloff, G., Giersch, W., Schulte-Elte, K.H., Vial, C., (1976) Helv. Chim. Acta, 59, p. 1140