Recent Results Toward The Stereoselective Synthesis Of Biologically Active Natural Products

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.792163172Dias, L.C., de Oliveira, L.G., Vilcachagua, J.D., Nigsch, F., (2005) J. Org. Chem, 70, p. 2225Dias, L.C., de Oliveira, L.G., (2001) Org. Lett, 3, p. 3951Dias, L.C., Meira, P.R.R., (2005) J. Org. Chem, 70, p. 4762Jansen, R., Washausen, P., Kunze, B., Reichenbach, H., Höfle, G., (1999) Eur. J. Org. Chem, 1085Kunze, B., Jansen, R., Höfle, G., Reichenbach, H., (1994) J. Antibiot, 47, p. 881Kunze, B., Jansen, R., Sasse, F., Höfle, G., Reichenbach, H., (1998) J. Antibiot, 51, p. 1075Total 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. 4989Total 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. 497Dias, L.C., de Oliveira, L.G., (2001) Org. Lett, 3, p. 3951Total 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. 2645Dias, L.C., de Oliveira, L.G., Vilcachagua, J.D., Nigsch, F., (2005) J. Org. Chem, 70, p. 2225Gurjar, M.K., Khaladkar, T.P., Borhade, R.G., Murugan, A., (2003) Tetrahedron Lett, 44, p. 5183. , For fragment synthesis, see: aRaghavan, S., Reddy, R., (2004) Tetrahedron Lett, 45, p. 5593Besev, M., Brehm, C., Fürstner, A., (2005) Collect. Czech. Chem. Commun, 70, p. 1696Yadav, J.S., Reddy, P.V., Chandraiah, L., (2007) Tetrahedron Lett, 48, p. 145Isobe, M., Kitamura, M., Mio, S., Goto, T., (1982) Tetrahedron Lett, 23, p. 221Kitamura, M., Isobe, M., Ichikawa, Y., Goto, Y., (1984) J. Org. Chem, 49, p. 3517Maruyama, K., Ueda, M., Sasaki, S., Iwata, Y., Miyazawa, M., Miyashita, M., (1998) Tetrahedron Lett, 39, p. 4517Jiang, L., Job, G.E., Klapars, A., Buchwald, S.P., (2003) Org. Lett, 5, p. 3667Pan, X., Cai, Q., Ma, D., (2004) Org. Lett, 6, p. 1809Kobayashi, M., Higuchi, K., Murakami, N., Tajima, H., Aoki, S., (1997) Tetrahedron Lett, 38, p. 2859Murakami, N., Wang, W., Aoki, M., Tsutsui, Y., Higuchi, K., Aoki, S., Kobayashi, M., (1997) Tetrahedron Lett, 38, p. 5533Hamamoto, T., Seto, H., Beppu, T., (1983) J. Antibiot, 36, p. 646Absolute 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: aCrimmins, M.T., King, B.W., (1998) J. Am. Chem. Soc, 120, p. 9084Smith III, A.B., Brandt, B.M., (2001) Org. Lett, 3, p. 1685Kalesse, M., Quitschalle, M., Khandavalli, C.P., Saeed, A., (2001) Org. Lett, 3, p. 3107Vicario, J.L., Job, A., Wolberg, M., Müller, M., Enders, D., (2002) Org. Lett, 4, p. 1023Marshall, J.A., Bourbeau, M.P., (2002) J. Org. Chem, 67, p. 2751Lautens, M., Stammers, T.A., (2002) Synthesis, 1993Kalesse, M., Chary, K.P., Quitschalle, M., Burzlaff, A., Kasper, C., Scheper, T., (2003) Chem. Eur. J, 9, p. 1129Languie, N.F., Panek, J.S., (2004) Org. Lett, 6, p. 3203Murakami, N., Sugimoto, M., Kobayashi, M., (2001) Bioorg. Med. Chem, 9, p. 57Murakami, N., Sugimoto, M., Nakajima, T., Kawanishi, M., Tsutsui, Y., Kobayashi, M., (2000) Bioorg. Med. Chem, 8, p. 2651Kalesse, M., Christmann, M., (2002) Synthesis, 981. , For a very interesting review about the chemistry and biology of the leptomycin family, seeDias, L.C., Meira, P.R.R., (2002) Tetrahedron Lett, 43, p. 185Dias, L.C., Meira, P.R.R., (2002) Tetrahedron Lett, 43, p. 8883Gage, J.R., Evans, D.A., (1990) Org. Synth, 68, p. 83Evans, D.A., Bartroli, J., Shih, T.L., (1981) J. Am. Chem. Soc, 103, p. 2127Evans, D.A., Taber, T.R., (1980) Tetrahedron Lett, 21, p. 4675Nagaoka, H., Kishi, Y., (1981) Tetrahedron, 37, p. 3873Lipshutz, B.H., Kozlowski, J., Wilhelm, R.S., (1982) J. Am. Chem. Soc, 104, p. 2305Kigoshi, H., Suenaga, K., Mutou, T., Ishigaki, T., Atsumi, T., Ishiwata, H., Sakakura, A., Yamada, K., (1996) J. Org. Chem, 61, p. 5326Takai, K., Nitta, K., Utimoto, K., (1986) J. Am. Chem. Soc, 108, p. 7408Marshall, J.A., Lu, Z.H., Johns, B.A., (1998) J. Org. Chem, 63, p. 817Marshall, J.A., Johns, B.A., (1998) J. Org. Chem, 63, p. 7885Miyaura, N., Suzuki, A., (1995) Chem. Rev, 95, p. 2457Johnson, C.R., Braun, M.P., (1993) J. Am. Chem. Soc, 115, p. 11014Dess, D.B., Martin, J.C., (1991) J. Am. Chem. Soc, 113, p. 7277Dess, D.B., Martin, J.C., (1983) J. Org. Chem, 48, p. 4155Ireland, R.E., Liu, L., (1993) J. Org. Chem, 58, p. 289