Pure and Applied Chemistry

Pure Appl. Chem., 2009, Vol. 81, No. 2, pp. 169-180

http://dx.doi.org/10.1351/PAC-CON-08-09-17

Total synthesis of novel dictyostatin analogs and hybrids as microtubule-stabilizing anticancer agents

References

• 1. D. J. Newman, G. M. Cragg. J. Nat. Prod. 70, 461 (2007). (http://dx.doi.org/10.1021/np068054v)
• 2. (a). I. Paterson, E. A. Anderson. Science 310, 451 (2005); (http://dx.doi.org/10.1126/science.1116364)
• 2. (b). K.-S. Yeung, I. Paterson. Chem. Rev. 105, 4237 (2005). (http://dx.doi.org/10.1021/cr040614c)
• 3. (a). T. Bergstralh, J. P. Y. Ting. Cancer Treat. Rev. 32, 166 (2006); (http://dx.doi.org/10.1016/j.ctrv.2006.01.004)
• 3. (b). M. Kavallaris, N. M. Verrills, B. T. Hill. Drug Resist. Update 4, 392 (2001); (http://dx.doi.org/10.1054/drup.2002.0230)
• 3. (c). K. H. Altmann, J. Gertsch. Nat. Prod. Rep. 24, 327 (2007); (http://dx.doi.org/10.1039/b515619j)
• 3. (d). I. E. L. M. Kuppens. Curr. Clin. Pharmacol. 1, 57 (2006). (http://dx.doi.org/10.2174/157488406775268200)
• 4. M. A. Jordan, L. Wilson. Nat. Rev. Cancer 4, 253 (2004). (http://dx.doi.org/10.1038/nrc1317)
• 5. (a). E. B. Watkins, A. G. Chittiboyina, J. C. Jung, M. A. Avery. Curr. Pharm. Design 11, 1615 (2005); (http://dx.doi.org/10.2174/1381612053764742)
• 5. (b). <http://www.fda.gov/bbs/topics/NEWS/2007/NEW01732.html>.
• 6. (a). A. B. Smith, B. S. Freeze. Tetrahedron 64, 261 (2008); (http://dx.doi.org/10.1016/j.tet.2007.10.039)
• 6. (b). G. J. Florence, N. M. Gardner, I. Paterson. Nat. Prod. Rep. 25, 342 (2008); (http://dx.doi.org/10.1039/b705661n)
• 6. (c). I. Paterson, G. J. Florence. Eur. J. Org. Chem. 2193 (2003). (http://dx.doi.org/10.1002/ejoc.200300061)
• 7. S. J. Mickel, D. Niederer, R. Daeffler, A. Osmani, E. Kuesters, E. Schmid, K. Schaer, R. Gamboni, W. C. Chen, E. Loeser, F. R. Kinder, K. Konigsberger, K. Prasad, T. M. Ramsey, J. Repic, R. M. Wang, G. Florence, I. Lyothier, I. Paterson. Org. Process Res. Dev. 8, 122 (2004), and preceding papers. (http://dx.doi.org/10.1021/op034134j)
• 8. (a). G. R. Pettit, Z. A. Cichacz, F. Gao, M. R. Boyd, J. M. Schmidt. J. Chem. Soc., Chem. Commun. 1111 (1994); (http://dx.doi.org/10.1039/c39940001111)
• 8. (b). R. A. Isbrucker, J. Cummins, S. A. Pomponi, R. E. Longley, A. E. Wright. Biochem. Pharmacol. 66, 75 (2003); (http://dx.doi.org/10.1016/S0006-2952(03)00192-8)
• 8. (c). I. Paterson, R. Britton, O. Delgado, A. E. Wright. Chem. Commun. 632 (2004). (http://dx.doi.org/10.1039/b316390c)
• 9. (a). I. Paterson, R. Britton, O. Delgado, A. Meyer, K. G. Poullennec. Angew. Chem., Int. Ed. 43, 462 (2004); (http://dx.doi.org/10.1002/anie.200352418)
• 9. (b). Y. Shin, J. H. Fournier, Y. Fukui, A. M. Bruckner, D. P. Curran. Angew. Chem., Int. Ed. 43, 4634 (2004); (http://dx.doi.org/10.1002/anie.200460593)
• 9. (c). Y. Shin, J. H. Fournier, A. Bruckner, C. Madiraju, R. Balachandran, B. S. Raccor, M. C. Edler, E. Hamel, R. P. Sikorski, A. Vogt, B. W. Day, D. P. Curran. Tetrahedron 63, 8537 (2007). (http://dx.doi.org/10.1016/j.tet.2007.05.033)
• 10. (a). R. M. Buey, I. Barasoain, E. Jackson, A. Meyer, P. Giannakakou, I. Paterson, S. Mooberry, J. M. Andreu, J. F. Diaz. Chem. Biol. 12, 1269 (2005); (http://dx.doi.org/10.1016/j.chembiol.2005.09.010)
• 10. (b). C. Madiraju, M. C. Edler, E. Hamel, B. S. Raccor, R. Balachandran, G. Zhu, K. A. Giuliano, A. Vogt, Y. Shin, J. H. Fournier, Y. Fukui, A. M. Bruckner, D. P. Curran, B. W. Day. Biochemistry 44, 15053 (2005); (http://dx.doi.org/10.1021/bi050685l)
• 10. (c). E. Hamel, B. W. Day, J. H. Miller, M. K. Jung, P. T. Northcote, A. K. Ghosh, D. P. Curran, M. Cushman, K. C. Nicolaou, I. Paterson, E. J. Sorensen. Mol. Pharmacol. 70, 1555 (2006). (http://dx.doi.org/10.1124/mol.106.027847)
• 11. A. Canales, R. Matesanz, N. M. Gardner, J. M. Andreu, I. Paterson, J. F. Diaz, J. Jimenez-Barbero. Chem.Eur. J. 14, 7557 (2008). (http://dx.doi.org/10.1002/chem.200800039)
• 12. V. M. Sanchez-Pedregal, K. Kubicek, J. Meiler, I. Lyothier, I. Paterson, T. Carlomagno. Angew. Chem., Int. Ed. 45, 7388 (2006). (http://dx.doi.org/10.1002/anie.200602793)
• 13. (a). I. Paterson, N. M. Gardner, K. G. Poullennec, A. E. Wright. Bioorg. Med. Chem. Lett. 17, 2443 (2007); (http://dx.doi.org/10.1016/j.bmcl.2007.02.031)
• 13. (b). I. Paterson, N. M. Gardner, K. G. Poullennec, A. E. Wright. J. Nat. Prod. 71, 364 (2008); (http://dx.doi.org/10.1021/np070547s)
• 13. (c). I. Paterson, N. M. Gardner, E. Guzman, A. E. Wright. Bioorg. Med. Chem. (2008), accepted;
• 13. (d). I. Paterson, N. M. Gardner, E. Guzman, A. E. Wright. Bioorg. Med. Chem. Lett. 18, 6268 (2008). (http://dx.doi.org/10.1016/j.bmcl.2008.09.109)
• 14. (a). Y. Shin, J. H. Fournier, R. Balachandran, C. Madiraju, B. S. Raccor, G. Zhu, M. C. Edler, E. Hamel, B. W. Day, D. P. Curran. Org. Lett. 7, 2873 (2005); (http://dx.doi.org/10.1021/ol050808u)
• 14. (b). Y. Fukui, A. M. Bruckner, Y. Shin, R. Balachandran, B. W. Day, D. P. Curran. Org. Lett. 8, 301 (2006); (http://dx.doi.org/10.1021/ol0526827)
• 14. (c). W. H. Jung, C. Harrison, Y. Shin, J. H. Fournier, R. Balachandran, B. S. Raccor, R. P. Sikorski, A. Vogt, D. P. Curran, B. W. Day. J. Med. Chem. 50, 2951 (2007); (http://dx.doi.org/10.1021/jm061385k)
• 14. (d). B. S. Raccors, A. Vogt, R. P. Sikorski, C. Madiraju, R. Balachandran, K. Montgomery, Y. Shin, Y. Fukui, W. H. Jung, D. P. Curran, B. W. Day. Mol. Pharmacol. 73, 718 (2008). (http://dx.doi.org/10.1124/mol.107.042598)
• 15. (a). W. C. Still, C. Gennari. Tetrahedron Lett. 24, 4405 (1983); (http://dx.doi.org/10.1016/S0040-4039(00)85909-2)
• 15. (b). I. Paterson, I. Lyothier. Org. Lett. 6, 4933 (2004); (http://dx.doi.org/10.1021/ol0478842)
• 15. (c). I. Paterson, I. Lyothier. J. Org. Chem. 70, 5494 (2005). (http://dx.doi.org/10.1021/jo050481a)
• 16. L. A. Martello, M. J. LaMarche, L. F. He, T. J. Beauchamp, A. B. Smith, S. B. Horwitz. Chem. Biol. 8, 843 (2001). (http://dx.doi.org/10.1016/S1074-5521(01)00055-2)
• 17. (a). I. Paterson, G. J. Florence, K. Gerlach, J. P. Scott. Angew. Chem., Int. Ed. 39, 377 (2000); (http://dx.doi.org/10.1002/(SICI)1521-3773(20000117)39:2<377::AID-ANIE377>3.0.CO;2-E)
• 17. (b). I. Paterson, G. J. Florence, K. Gerlach, J. P. Scott, N. Sereinig. J. Am. Chem. Soc. 123, 9535 (2001); (http://dx.doi.org/10.1021/ja011211m)
• 17. (c). I. Paterson, O. Delgado, G. J. Florence, I. Lyothier, J. P. Scott, N. Sereinig. Org. Lett. 5, 35 (2003); (http://dx.doi.org/10.1021/ol0270780)
• 17. (d). I. Paterson, O. Delgado, G. J. Florence, I. Lyothier, M. O'Brien, J. P. Scott, N. Sereinig. J. Org. Chem. 70, 150 (2005). (http://dx.doi.org/10.1021/jo048534w)
• 18. (a). R. A. Isbrucker, S. P. Gunasekera, R. E. Longley. Cancer Chemother. Pharmacol. 48, 29 (2001); (http://dx.doi.org/10.1007/s002800100287)
• 18. (b). S. P. Gunasekera, R. E. Longley, R. A. Isbrucker. J. Nat. Prod. 65, 1830 (2002). (http://dx.doi.org/10.1021/np0203234)
• 19. W. S. Mahoney, D. M. Brestensky, J. M. Stryker. J. Am. Chem. Soc. 110, 291 (1998). (http://dx.doi.org/10.1021/ja00209a048)
• 20. (a). A. K. Chatterjee, T. L. Choi, D. P. Sanders, R. H. Grubbs. J. Am. Chem. Soc. 125, 11360 (2003); (http://dx.doi.org/10.1021/ja0214882)
• 20. (b). S. H. Hong, D. P. Sanders, C. W. Lee, R. H. Grubbs. J. Am. Chem. Soc. 127, 17160 (2005). (http://dx.doi.org/10.1021/ja052939w)
• 21. (a). I. Paterson, N. M. Gardner. Chem. Commun. 49 (2007); (http://dx.doi.org/10.1039/b615122a)
• 21. (b). I. Paterson, G. J. Naylor, A. E. Wright. Chem. Commun. 4628 (2008). (http://dx.doi.org/10.1039/b811575c)
• 22. Y. Shin, N. Choy, R. Balachandran, C. Madiraju, B. W. Day, D. P. Curran. Org. Lett. 4, 4443 (2002). (http://dx.doi.org/10.1021/ol026942l)
• 23. I. Paterson, D. J. Wallace, C. J. Cowden. Synthesis 639 (1998). (http://dx.doi.org/10.1055/s-1998-5929)