Actas de congresos
Recent Results Toward The Stereoselective Synthesis Of Biologically Active Natural Products
Registro en:
Pure And Applied Chemistry. , v. 79, n. 2, p. 163 - 172, 2007.
334545
10.1351/pac200779020163
2-s2.0-33846930622
Autor
Dias L.C.
De Oliveira L.G.
Meira P.R.R.
Institución
Resumen
This paper describes the convergent and stereocontrolled asymmetric total synthesis of (+)-crocacins C and D, potent inhibitors of animal cell cultures and several yeasts and fungi, and (-)-callystatin A, a potent antitumor polyketide. © 2007 IUPAC. 79 2 163 172 Dias, L.C., de Oliveira, L.G., Vilcachagua, J.D., Nigsch, F., (2005) J. Org. Chem, 70, p. 2225 Dias, L.C., de Oliveira, L.G., (2001) Org. Lett, 3, p. 3951 Dias, L.C., Meira, P.R.R., (2005) J. Org. Chem, 70, p. 4762 Jansen, R., Washausen, P., Kunze, B., Reichenbach, H., Höfle, G., (1999) Eur. J. Org. Chem, 1085 Kunze, B., Jansen, R., Höfle, G., Reichenbach, H., (1994) J. Antibiot, 47, p. 881 Kunze, B., Jansen, R., Sasse, F., Höfle, G., Reichenbach, H., (1998) J. Antibiot, 51, p. 1075 Total synthesis of (+)-crocacin A: (a) J. T. Feutrill, M. A. Rizzacasa. Aust. J. Chem. 56, 783 (2003);Chakraborty, T.K., Laxman, P., (2003) Tetrahedron Lett, 44, p. 4989 Total synthesis of (+)-crocacin C: (a) J. T. Feutrill, M. J. Lilly, M. A. Rizzacasa. Org. Lett. 2, 3365 (2000);Chakraborty, T.K., Jayaprakash, S., (2001) Tetrahedron Lett, 42, p. 497 Dias, L.C., de Oliveira, L.G., (2001) Org. Lett, 3, p. 3951 Total synthesis of (+)-crocacin D: (a) J. T. Feutrill, M. J. Lilly, M. A. Rizzacasa. Org. Lett. 4, 525 (2002);Chakraborty, T.K., Laxman, P., (2002) Tetrahedron Lett, 43, p. 2645 Dias, L.C., de Oliveira, L.G., Vilcachagua, J.D., Nigsch, F., (2005) J. Org. Chem, 70, p. 2225 Gurjar, M.K., Khaladkar, T.P., Borhade, R.G., Murugan, A., (2003) Tetrahedron Lett, 44, p. 5183. , For fragment synthesis, see: a Raghavan, S., Reddy, R., (2004) Tetrahedron Lett, 45, p. 5593 Besev, M., Brehm, C., Fürstner, A., (2005) Collect. Czech. Chem. Commun, 70, p. 1696 Yadav, J.S., Reddy, P.V., Chandraiah, L., (2007) Tetrahedron Lett, 48, p. 145 Isobe, M., Kitamura, M., Mio, S., Goto, T., (1982) Tetrahedron Lett, 23, p. 221 Kitamura, M., Isobe, M., Ichikawa, Y., Goto, Y., (1984) J. Org. Chem, 49, p. 3517 Maruyama, K., Ueda, M., Sasaki, S., Iwata, Y., Miyazawa, M., Miyashita, M., (1998) Tetrahedron Lett, 39, p. 4517 Jiang, L., Job, G.E., Klapars, A., Buchwald, S.P., (2003) Org. Lett, 5, p. 3667 Pan, X., Cai, Q., Ma, D., (2004) Org. Lett, 6, p. 1809 Kobayashi, M., Higuchi, K., Murakami, N., Tajima, H., Aoki, S., (1997) Tetrahedron Lett, 38, p. 2859 Murakami, N., Wang, W., Aoki, M., Tsutsui, Y., Higuchi, K., Aoki, S., Kobayashi, M., (1997) Tetrahedron Lett, 38, p. 5533 Hamamoto, T., Seto, H., Beppu, T., (1983) J. Antibiot, 36, p. 646 Absolute stereochemistry and synthesis of leptomycin B: M. Kobayashi, W. Wang, Y. Tsutsui, M. Sugimoto, N. Murakami. Tetrahedron Lett. 39, 8291 (1998)Murakami, N., Wang, W., Aoki, M., Tsutsui, Y., Sugimoto, M., Kobayashi, M., (1998) Tetrahedron Lett, 39, p. 2349. , For total syntheses of callystatin A, see: a Crimmins, M.T., King, B.W., (1998) J. Am. Chem. Soc, 120, p. 9084 Smith III, A.B., Brandt, B.M., (2001) Org. Lett, 3, p. 1685 Kalesse, M., Quitschalle, M., Khandavalli, C.P., Saeed, A., (2001) Org. Lett, 3, p. 3107 Vicario, J.L., Job, A., Wolberg, M., Müller, M., Enders, D., (2002) Org. Lett, 4, p. 1023 Marshall, J.A., Bourbeau, M.P., (2002) J. Org. Chem, 67, p. 2751 Lautens, M., Stammers, T.A., (2002) Synthesis, 1993 Kalesse, M., Chary, K.P., Quitschalle, M., Burzlaff, A., Kasper, C., Scheper, T., (2003) Chem. Eur. J, 9, p. 1129 Languie, N.F., Panek, J.S., (2004) Org. Lett, 6, p. 3203 Murakami, N., Sugimoto, M., Kobayashi, M., (2001) Bioorg. Med. Chem, 9, p. 57 Murakami, N., Sugimoto, M., Nakajima, T., Kawanishi, M., Tsutsui, Y., Kobayashi, M., (2000) Bioorg. Med. Chem, 8, p. 2651 Kalesse, M., Christmann, M., (2002) Synthesis, 981. , For a very interesting review about the chemistry and biology of the leptomycin family, see Dias, L.C., Meira, P.R.R., (2002) Tetrahedron Lett, 43, p. 185 Dias, L.C., Meira, P.R.R., (2002) Tetrahedron Lett, 43, p. 8883 Gage, J.R., Evans, D.A., (1990) Org. Synth, 68, p. 83 Evans, D.A., Bartroli, J., Shih, T.L., (1981) J. Am. Chem. Soc, 103, p. 2127 Evans, D.A., Taber, T.R., (1980) Tetrahedron Lett, 21, p. 4675 Nagaoka, H., Kishi, Y., (1981) Tetrahedron, 37, p. 3873 Lipshutz, B.H., Kozlowski, J., Wilhelm, R.S., (1982) J. Am. Chem. Soc, 104, p. 2305 Kigoshi, H., Suenaga, K., Mutou, T., Ishigaki, T., Atsumi, T., Ishiwata, H., Sakakura, A., Yamada, K., (1996) J. Org. Chem, 61, p. 5326 Takai, K., Nitta, K., Utimoto, K., (1986) J. Am. Chem. Soc, 108, p. 7408 Marshall, J.A., Lu, Z.H., Johns, B.A., (1998) J. Org. Chem, 63, p. 817 Marshall, J.A., Johns, B.A., (1998) J. Org. Chem, 63, p. 7885 Miyaura, N., Suzuki, A., (1995) Chem. Rev, 95, p. 2457 Johnson, C.R., Braun, M.P., (1993) J. Am. Chem. Soc, 115, p. 11014 Dess, D.B., Martin, J.C., (1991) J. Am. Chem. Soc, 113, p. 7277 Dess, D.B., Martin, J.C., (1983) J. Org. Chem, 48, p. 4155 Ireland, R.E., Liu, L., (1993) J. Org. Chem, 58, p. 2899