Abstract
The total synthesis of epothilone D with six-fold application in the intermediate stages of successive cyclopropanation — opening or cleavage of the three-membered ring was performed. These transformations underlie the new stereoselective method developed for coupling fragments C7–C12 and C13–C21 in the target molecule.
Similar content being viewed by others
References
Hudlicky, T., Reed, J.W. Angew. Chem., Int. Ed., 2010, p. 49, p. 4864; Carson, C.A., Kerr, M.A. Chem. Soc. Rev., 2009, vol. 38, p. 3051; Salaun, J. Chem. Rev., 2005, vol. 105, p. 285; Brandi, A., Cicchi, S., Cordero, F.M., Goti, A. Chem. Rev., 2003, vol. 103, p. 1213; Fedorynski, M. Chem. Rev., 2003, vol. 103, p. 1099; Kulinkovich, O.G. Polish, J. Chem., 1997, p. 849; Kulinkovich, O.G., Usp. Khim., 1993, vol. 62, p. 887; Kostikov, R.R., Molchanov, A.P., and Hopf, H., Top. Curr. Chem., 1990, vol. 155, p. 41; Wong, H.N.C., Hon, M.Y., Tse, C.W., Yip, Y.C., Tanko, J., and Hudlicky, T., Chem. Rev., 1989, vol. 89, p. 165.
Kulinkovich, O.G., Chem. Rev., 2003, vol. 103, p. 2597; Gibson, D.H. and De Puy, C.H., Chem. Rev., 1974, vol. 74, p. 605.
Kulinkovich, O.G., Sviridov, S.V., Vasilevskii, D.A., and Pritytskaya, T.S., Zh. Org. Khim., 1989, vol. 25, p. 2245; Kulinkovich, O.G., Sviridov, S.V., Vasilevskii, D.A., and Pritytskaya, T.S., Synthesis, 1991, 234; Cviridov, S.V., Vasilevskii, D.A., and Kulinkovich, O.G., Zh. Org. Khim., 1991, vol. 27, p. 1431.
Kulinkovich, O.G., Savchenko, A.I., Sviridov, S.V., and Vasilevski, D.A., Mendeleev Commun., 1993, p. 230; Epstein, O.L., Savchenko, A.I., and Kulinkovich, O.G., Tetrahedron Lett., 1999, vol. 40, p. 5935; Epshtein, O.L., Savchenko, A.I., and Kulinkovich, O.G., Izv. Akad. Nauk, Ser. Khim., 2000, p. 376.
Wolan, A. and Six, Y., Tetrahedron, 2010, vol. 66, p. 15; Wolan, A. and Six, Y., Tetrahedron, 2010, vol. 66, p. 3097; Kulinkovich, O.G., Izv. Akad. Nauk, Ser. Khim., 2004, p. 1022; Kulinkovich, O.G. and de Meijere, A., Chem. Rev., 2000, vol. 100, p. 2789.
Kulinkovich, O.G., Eur. J. Org. Chem., 2004, p. 4517; Kovalenko, V.N., Masalov, N.V., and Kulinkovich, O.G., Zh. Org. Khim., 2009, vol. 45, p. 1318; Mineyeva, I.V. and Kulinkovich, O.G., Tetrahedron Lett., 2010, vol. 51, p. 1836; Kananovich, D.G., Zubrytski, D.M., and Kulinkovich, O.G., Synlett., 2010, p. 1043.
Nicolaou, K.C., Roschangar, F., and Vourloumis, D., Angew. Chem., 1998, vol. 110, p. 2120; Angew. Chem., Int. Ed. Engl., 1998, vol. 37, p. 2014; Harris, C.R. and Danishefsky, S.J., J. Org. Chem., 1999, vol. 64, p. 8434; Mulzer, J., Martin, H.J., and Berger, M., J. Heterocycl. Chem., 1999, vol. 36, p. 1421; Nicolaou, K.C., Ritzen, A., and Namoto, K., Chem. Commun., 2001, p. 1523; Altmann, K.-H., Org. Biomol. Chem., 2004, vol. 2, p. 2137; Watkins, E.B., Chittiboyina, A.G., Jung, J.C., and Avery, M.A., Curr. Pharm. Des., 2005, vol. 11, p. 1615; Watkins, E.B., Chittiboyina, A.G., and Avery, M.A., Eur. J. Org. Chem., 2006, p. 4071; Altmann, K.-H., Pfeiffer, B., Arseniyadis, S., Pratt, B.A., and Nicolaou, K.C., Chem. Med. Chem., 2007, vol. 2, p. 396; Feyen, F., Cachoux, F., Gertsch, J., Wartmann, M., and Altmann, K.-H., Acc. Chem. Res., 2008, vol. 41, p. 21; Mulzer, J., Altmann, K.-H., Hofl e, G., Muller, R., and Prantz, K., C. R. Chimie, 2008, vol. 11, p. 1336; Altmann, K.-H., Hofl e, G., Muller, R., Mulzer, J., and Prantz, K., The Epothilones: An Outstanding Family of Anti-Tumor Agents, New York: Springer, Wien, 2009.
Meng, D., Bertinato, P., Balog, A., Su, D.-S., Kamenecka, T., Sorensen, E.J., and Danishefsky, S.J., J. Am. Chem. Soc., 1997, vol. 119, p. 10073.
Nicolaou, K.C., Ninkovic, S., Sarabia, F., Vourloumis, D., He, Y., Vallberg, H., Finlay, M.R.V., Yang, Z. J. Am. Chem. Soc., 1997, vol. 119, p. 7974.
Balog, A., Harris, C., Savin, K., Zhang, X.-G., Chou, T.C., Danishefsky, S.J. Angew. Chem., Int. Ed. Engl., 1998, vol. 37, p. 2675.
May, S.A. and Grieco, P.A., Chem. Commun., 1998, p. 1597.
Schinzer, D., Bauer, A., and Schieber, J., Chem. Eur. J., 1999, vol. 5, p. 2492.
White, J.D., Carter, R.G., and Sundermann, K.F., J. Org. Chem., 1999, vol. 64, p. 684.
Mulzer, J., Mantoulidis, A., and Ohler, E., J. Org. Chem., 2000, vol. 65, p. 7456.
Taylor, R.E. and Chen, Y., Org. Lett., 2001, vol. 3, p. 2221.
Martin, N. and Thomas, E.J., Tetrahedron Lett., 2001, vol. 42, p. 8373.
Jung, J.-C., Kache, R., Vines, K.K., Zheng, Y.-S., Bijoy, P., Valluri, M., and Avery, M.A., J. Org. Chem., 2004, vol. 69, p. 9269.
Broadrup, R.L., Sundar, H.M., and Swindell, C.S., Bioorg. Chem., 2005, vol. 33, p. 116.
Keck, G.E., Giles, R.L., Cee, V.J., Wager, C.A., Yu, T., and Kraft, M.B., J. Org. Chem., 2008, vol. 73, p. 9675.
Hurski, A.L. and Kulinkovich, O.G., Tetrahedron Lett., 2010, vol. 51, p. 3497.
Nicolaou, K.C., Sarabia, F., Ninkovic, S., and Yang, Z., Angew. Chem., Int. Ed. Engl., 1997, vol. 36, p. 525.
Deno, N.C., J. Am. Chem. Soc., 1947, vol. 69, p. 2233.
Slougui, N. and Rousseau, G., Synth. Commun., 1987, vol. 17, p. 1.
Kiyooka, S. and Hena, M.A., J. Org. Chem., 1999, vol. 64, p. 5511.
Stahl, G.W. and Cottle, D.L., J. Am. Chem. Soc., 1943, vol. 65, p. 1782; De Puy, C.H. and Breitbeil, F.W., J. Am. Chem. Soc., 1963, vol. 85, p. 2176.
Kananovich, D.G., Hurski, A.L., and Kulinkovich, O.G., Tetrahedron Lett., 2007, vol. 48, p. ai]8424.
Kozyrkov, Yu.Yu. and Kulinkovich, O.G., Synlett., 2002, p. 443.
Ravid, U., Silverstain, R.M., and Smith, L.R., Tetrahedron, 1978, vol. 34, p. 1449.
Kulinkovich, O.G., Kozyrkov, Y.Y., Bekish, A.V., Matiushenkov, E.A., and Lysenko, I.L. Synthesis, 2005, p. 1713.
Hurski, A.L., Sokolov, N.A., and Kulinkovich, O.G., Tetrahedron., 2009, vol. 65, p. 3518.
Reddy, P.P., Yen, K.-F., and Uang, B.-J., J. Org. Chem., 2002, vol. 67, p. 1034.
Bekish, A.V., Isakov, V.E., and Kulinkovich, O.G., Tetrahedron Lett., 2005, vol. 46, p. 6979.
Kulinkovich, O.G. and Bagutskii, V.V., Zh. Org. Khim., 1997, vol. 33, p. 898.
Rubottom, G.M., Marrero, R., Krueger, D.S., and Schreiner, J.L., Tetrahedron Lett., 1977, vol. 18, p. 4013; Kirihara, M., Yokoyama, S., Kakuda, H., and Momose, T., Tetrahedron Lett., 1995, vol. 38, p. 6907; Kirihara, M., Yokoyama, S., Kakuda, H., and Momose, T., Tetrahedron, 1998, vol. 54, p. 13943.
Kulinkovich, O.G., Epstein, O.L., Isakov, V.E., and Khmelnitskaya, E.A., Synlett., 2001, p. 49.
Cha, J.K., Kim, H., and Lee, J., J. Am. Chem. Soc., 1996, vol. 118, p. 4198; Lee, J., Kim, Y.G., Bae, J.G., and Cha, J.K., J. Org. Chem., 1996, vol. 61, p. 4878;, Chem. Soc. Jpn., 1979, vol. 52, p. 1989.
Iranaga, J., Hirata, K., Saeki, H., Katsuki, T., and Yamaguchi, M., Bull. Chem. Soc. Jpn., 1979, vol. 52, p. 1989.
Dale, J.A., Dull, D.L., and Mosher, H.S., J. Org. Chem., 1969, vol. 34, p. 2543.
Author information
Authors and Affiliations
Corresponding author
Additional information
Dedicated to Academician O.M. Nefedov on occasion of his 80th anniversary
Original Russian Text © A.L. Hurski, O.G. Kulinkovich, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 11, pp. 1623–1642
Rights and permissions
About this article
Cite this article
Hurski, A.L., Kulinkovich, O.G. Synthesis of epothilone D with the forced application of oxycyclopropane intermediates. Russ J Org Chem 47, 1653–1674 (2011). https://doi.org/10.1134/S1070428011110029
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428011110029