Artículos de revistas
Stereoselective Synthesis Of Conformationally Restricted Analogues Of Aspartic And Glutamic Acids Front Endocyclic Enecarbamates
Registro en:
Tetrahedron Letters. , v. 38, n. 11, p. 1869 - 1872, 1997.
404039
10.1016/S0040-4039(97)00238-4
2-s2.0-0031575815
Autor
Carpes M.J.S.
Miranda P.C.M.L.
Correia C.R.D.
Institución
Resumen
The stereoselective synthesis of cyclic amino acids incorporating the care framework of aspartic acid and glutamic acids were accomplished from a common intermediate. Oxidative cleavage of an aza-bicyclic-dichlorocyclobutanone/pentanone with Me2CuLi/Ac2O followed by ozonolysis furnished the amino acid derivatives in good overall yields in a three-step sequence. This protocol was also applied to the synthesis of a cis-β-amino acid and to the enantioselective construction of a chimeric amino acid incorporating the basic skeleton of four different naturally occurring amino acids into a single structure. 38 11 1869 1872 Horwell, D.C., Nichols, P.D., Ratcliffe, G.S., Roberts, E., (1994) J. Org. Chem., 59, pp. 4418-4423 Mizutani, T., Murakami, T., Kurahashi, T., Ogoshi, H., (1996) J. Org. Chem., 61, pp. 539-648 Parsons, A.F., (1996) Tetrahedron, 52, pp. 4149-4174 Johnson, R.L., Koerner, J.F., (1988) J. Med. Chem., 31, pp. 2057-2066 Watkins, J.C., Krogsgaard-Larsen, P., Honoré, T., (1990) Trends Pharmacol. Sci., 11, pp. 25-33 Palfreyman, M.G., Reynolds, I.J., Skolnick, P., Direct and allosteric control of glutamate receptors (1994) Pharmacology and Toxicology Series, , Hollinger, M. A. Ed. CRC Press, Boca Raton Sutcliffe, M.J., Wo, Z.G., Oswald, R.E., (1996) Biophys. J., 70, pp. 1575-1589 Shimamoto, K., Ishida, M., Shinozaki, H., Ohfune, Y., (1991) J. Org. Chem., 56, pp. 4167-4176 Langlois, N., Andriamialisoa, R.Z., (1991) Tetrahedron Lett., 32, pp. 3057-3058 Langlois, N., Rojas, A., (1993) Tetrahedron Lett., 34, pp. 2477-2480 Sasaki, N.A., Pauly, R., Fontaine, C., Chiaroni, A., Riche, C., Potier, P., (1994) Tetrahedron Lett., 35, pp. 241-244 Agami, C., Kadouri-Puchot, C., Le Guen, V., Vaissermann, J., (1995) Tetrahedron Lett., 36, pp. 1657-1660 Baldwin, J.E., Bramford, S.J., Fryer, A.M., Wood, M.E., (1995) Tetrahedron Lett., 36, pp. 4869-4872. , and refs therein Lubell, W.D., Gill, P., (1995) J. Org. Chem, 60, pp. 2658-2659 Sharma, R., Lubell, W.D., (1996) J. Org. Chem., 61, pp. 202-209 (1996) 11th International Conference on Organic Synthesis, , Amsterdam, The Netherlands, June 30-July 4, PO-75 Faria, A.R., Matos, C.R.R., Correia, C.R.D., (1993) Tetrahedron Lett., 34, pp. 27-30 Deprés, J.-P., Coelho, F.A.S., Greene, A.E., (1985) J. Org. Chem., 50, pp. 1972-1973 Deprés, J.-P., Greene, A.E., (1989) Tetrahedron Lett., 30, pp. 7065-7068 Humphrey, J.M., Bridges, R.J., Hart, J.A., Chamberlin, A.R., (1994) J. Org. Chem., 59, pp. 2467-2472 Baldwin, J.E., Adlington, R.M., Gollins, D.W., Godfrey, C.R.A., (1995) Tetrahedron, 51, pp. 5169-5180 Cotton, R., Johnstone, A.N.C., North, M., (1995) Tetrahedron, 51, pp. 8525-8544. , and references cited therein. All spectroscopic data obtained were in very good agreement with those reported. Note: after completion of the work presented in Scheme 1 we performed the conversion of 7 into 8 and 11 into 13 using acid hydrolysis (HCl 6M) in 90% and 87% yields respectively. However, some epimerization has been observed in these cases Shono, T., Matsumura, Y., Tsubata, K., Sugihara, Y., Yamane, S., Kamazawa, T., Aoki, T., (1982) J. Am. Chem. Soc., 104, pp. 6697-6703. , We recently developed an alternative methodology for the preparation of optically pure five-membered endocyclic enecarbamates starting from (S)-pyroglutamic acid. A full account of this work will be presented in due course note