Design and synthesis C6-C8 bridged epothilone a

Organic Letters

Volumn 10, Issue 8, 2008, Pages 1565-1568

  Zhan, Weiqiang ^a   Jiang, Yi ^a   Brodie, Peggy J ^b   Kingston, David G I ^b   Liotta, Dennis C ^a   Snyder, James P ^a  

^a EMORY UNIVERSITY   (United States)

^b VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOTHILONE A; EPOTHILONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; DRUG SCREENING; FEMALE; HUMAN; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; EPOTHILONES; FEMALE; HUMANS; MODELS, MOLECULAR;

EID: 44449113900     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800422q     Document Type: Article

References (52)

1. (a) Gerth, K.; Bedorf, N.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560.
2. (b) Höfle, G. H.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1567.
3. For a review of the chemical biology of epothilones, see: Nicolaou, K. C; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2015.
4. Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M.; Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325.
5. (a) Giannakakou, P.; Sackett, D. L.; Kang, Y. K.; Zhan, Z.; Buters, J. T.; Fojo, T.; Poruchynsky, M. S. J. Biol. Chem. 1997, 272, 17118.
6. (b) Kowalski, R. J.; Giannakakou, P.; Hamel, E. J. Biol. Chem. 1997, 272, 2534.
7. (c) Altmann, K. H.; Wartmann, M.; O'Reilly, T. Biochim. Biophys. Acta 2000, 1470, M79.
8. (d) Wartmann, M.; Altmann, K. H. Curr. Med. Chem. Anticancer Agents 2002, 2, 123.
9. For recent general reviews, see:
10. (a) Altmann, K. H.; Florsheimer. A.; Bold, G.; Caravatti, G.; Wartmann, M. Chimia 2004, 58, 686.
11. (b) Altmann, K. H. Cur. Pharm. Des. 2005, 11, 1595.
12. (c) Altmann, K. H.; Pfeiffer, B.; Arseniyadis, S.; Pratt, B. A.; Nicolaou, K. C. Chemmedchem 2007, 2, 396.
13. (d) Feyen, F.; Cachoux, R; Gertsch, J.; Wartmann, M.: Altmann, K. Acc. Chem. Res. 2008, 41, 21.
14. For recent reviews on the synthesis of epothilones and analogs, see:
15. (a) Rivkin, A.; Cho, Y. S.; Gabarda, A. E.; Yoshimura, F.; Danishefsky, S J. J. Nat. Prod. 2004, 67, 139.
16. (b) Luduvico, I.; Le Hyaric, M.; De Almeida. M. V.; Da, Silva, A. D. Mini-Rev. Org. Chem. 2006, 3, 49.
17. (c) Watkins, E. B.; Chittiboyina, A. G.; Avery, M. A. Eur. J. Org. Chem. 2006, 4071.
18. (a) Nicolaou, K. C; Vourloumis, D.; Li, T. H.; Pastor, J.; Winssinger N.; He, Y.; Ninkovic, S.; Sarabia, F.; Vallberg, H.; Roschangar, F.; King. N. P.; Finlay, M. R. V.; Giannakakou, P.; VerdierPinard, P.; Hamel, E Angew. Chem., Int. Ed. Engl. 1997, 36, 2097.
19. (b) Su, D. S.; Balog, A.; Meng, D. F.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y. H.; Chou, T. C.; He, L. F.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 2093. (c; For reviews, see: ref 5c.
20. (a) Carlomagno, T.; Blommers, M. J. J.; Meiler, J.; Jahnke, W. Schupp, T.; Petersen, F.; Schinzer, D.; Altmann, K. H.; Griesinger, C. Angew. Chem., Int. Ed. 2003, 42, 2511.
21. (b) Taylor, R. E.; Chen, Y.; Beatty A.; Myles, D. C; Zhou, Y. Q. J. Am. Chem. Soc. 2003, 125, 26.
22. (c) Heinz, D. W.; Schubert, W. D.; Hofle, G. Angew. Chem., Int. Ed. 2005, 44, 1298
23. (d) For reviews, see: ref 5c.
24. Nettles, J. H.; Li, H. L.; Cornett, B.; Krahn, J. M.; Snyder, J. P.: Downing, K. H. Science 2004, 305, 866.
25. (a) Klar, U.; Buchmann, B.; Schwede, W.; Skuballa, W.; Hoffinann. J.; Lichtner, R. B. Angew. Chem., Int. Ed. 2006, 45, 7942.
26. (b) Conlin, A.; Former, M.; Hudis, C; Kar, S.; Kirkpatrick, P. Nat. Rev. Drug Discover) 2007, 6, 953.
27. MacroModel 9.0 (Maestro 7.0 interface), supplied by Schrodinger. Portland, OR; www.schrodinger.com
28. Regueiro-Ren, A.; Leavitt, K.; Kim, S. H.; Hofle, G.; Kiffe, M.; Gougoutas, J. Z.; DiMarco, J. D.; Lee, F. Y. F.; Fairchild, C. R.; Long, B. H.; Vite, G. D. Org. Lett. 2002, 4, 3815.
29. Martin, H. J.; Pojarliev, P.; Kahlig, H.; Mulzer, J. Chem. Eur. J. 2001, 7, 2261.
30. (a) Meng, D. F.; Bertinato, P.; Balog, A.; Su, D. S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073.
31. (b) Chemler, S. R.; Trauner, D.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 4544.
32. (a) For a review of substrate directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307. For substituent directed epoxide opening, see:
33. (b) Flippin, L. A.; Brown, P. A.; Jalaliaraghi, K. J. Org. Chem. 1989, 54, 3588.
34. (c) Chini, M.; Crotti, P.; Flippin, L. A.; Gardelli, C; Macchia, F. J. Org. Chem. 1992, 57, 1713.
35. (a) Brown, H. C; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1985, 107, 2564.
36. (b) Brown, H. C; Bhat, K. S.; Jadhav, P. K. J. Chem. Soc. Perkin Trans. 1 1991, 2633.
37. Richter, F.; Bauer, M.; Perez, C; Maichle-Mossmer, C; Maier, M. E. J. Org. Chem. 2002, 67, 2474.
38. (a) Jadhav, P. K.; Bhat, K. S.; Perumal, P. T.; Brown, H. C. J. Org. Chem. 1986, 51, 432.
39. (b) Nicolaou, K. C; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 7974.
40. (a) Lin, M. Y.; Das, A.; Liu, R. S. J. Am. Chem. Soc. 2006, 128, 9340.
41. (b) Takenaka, Y.; Ito, H.; Iguchi, K. Tetrahedron 2007, 63, 510.
42. Nelson, T. D.; Crouch, R. D. Synthesis 1996, 1031.
43. (a) Mihelich, E. D.; Daniels, K.; Eickhoff, D. J. J. Am. Chem. Soc. 1981, 103, 7690.
44. (b) Bolm, C. Coord. Chem. Rev. 2003, 237, 245.
45. Carre, M. C; Houmounou, J. P.; Caubere, P. Tetrahedron Lett. 1985, 26, 3107.
46. Eliel, E. L.; Allinger, N. L.; Angyal, S. J.; Morrison, G. A. Conformational Analysis; Interscience: New York, 1965; p 102.
47. For Sharpless asymmetric dihydroxylation rate of substituted olefins, see:
48. (a) Andersson, P. G.; Sharpless, K. B. J. Am. Chem. Soc. 1993, 115, 7047.
49. (b) For a review, see: Becker, H.; Soler, M. A.; Sharpless, K. B. Tetrahedron 1995, 51, 1345.
50. Bal, B. S.; Childers, W. E.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
51. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 2173.
52. Tang, L.; Shah, S.; Chung, L.; Carney, J.; Katz, L.; Khosla, C; Mien, B. Science 2000, 287, 640.