Synthesis of epothilone analogues by antibody-catalyzed resolution of thiazole aldol synthons on a multigram scale. Biological consequences of C-13 alkylation of epothilones

ChemBioChem

Volumn 2, Issue 9, 2001, Pages 656-665

  Sinha, Subhash C ^a,b   Sun, Jian ^a   Wartmann, Markus ^a   Lerner, Richard A ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODY; ANTINEOPLASTIC AGENT; EPOTHILONE C; EPOTHILONE DERIVATIVE; LACTONE; LYASE; MACROLIDE; THIAZOLE DERIVATIVE; TUBULIN;

ALKYLATION; ANIMAL; ARTICLE; BIOSYNTHESIS; CATALYSIS; CELL CULTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; HUMAN; IMMUNOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SWINE; SYNTHESIS;

ALDEHYDE-LYASES; ALKYLATION; ANIMALS; ANTIBODIES; ANTINEOPLASTIC AGENTS; CATALYSIS; EPOTHILONES; HUMANS; LACTONES; MACROLIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; STEREOISOMERISM; SWINE; THIAZOLES; TUBULIN; TUMOR CELLS, CULTURED;

EID: 0035802133     PISSN: 14394227     EISSN: None     Source Type: Journal    
DOI: 10.1002/1439-7633(20010903)2:9<656::AID-CBIC656>3.0.CO;2-3     Document Type: Article

References (39)

1. a) D. M. Bollag, P. A. McQueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides, C. M. Woods, Cancer Res. 1995, 55, 2325;
2. b) K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1996, 49, 560;
3. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671;
4. Angew. Chem. Int. Ed. Engl. 1996, 35, 1567.
5. For reviews describing most of the early works, see: a) K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120;
6. Angew. Chem. Int. Ed. 1998, 37, 2014;
7. b) K.C. Nicolaou, M.R.V. Finlay, S. Ninkovic, N.P. King, Y. He, T. Li, F. Sarabia, D. Vourloumis, Chem. Biol. 1998, 5, 365;
8. G. Appendino, G. Casiraghi, Chemtracts: Org. Chem. 1998, 11, 678;
9. S. B. Buck, S. F. Victory, R. H. Himes, G. I. Georg, Chemtracts: Org. Chem. 1998, 11, 671 ;
10. e) K. C. Nicolaou, D. Hepworth, N. P. King, M. R. V. Finlay, Pure Appl. Chem. 1999, 71, 989;
11. f) C.R. Harris, S.J. Danishefsky, J. Org. Chem. 1999, 64, 8434;
12. g) J. Mulzer, Monatsh. Chem. 2000, 131, 205;
13. h) L. A. Wessjohann, Curr. Opin. Chem. Biol. 2000, 4, 303;
14. K.-H. Altmann, M. Wartmann, T. O'Reilly, Biochim. Biophys. Acta. 2000, 1470, M79-M91, and references therein.
15. a) C. Harris, S. D. Kuduk, A. Balog, K. Savin, P. W. Glunz, S. J. Danishefsky, J. Am. Chem. Soc. 1999, 121, 7050;
16. b) M. D. Chappell, S. J. Stachel, C. B. Lee, S.J. Danishefsky, Org. Lett. 2000, 2, 1633;
17. K.C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, F. Roschangar, F. Sarabia, S. Ninkovic, Z. Yang, J. I. Trujillo, J. Am. Chem. Soc. 1997, 119, 7960;
18. K. C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M. R. V. Finlay, Z. Yang, J. Am. Chem. Soc. 1997, 119, 7974;
19. e) D. Schinzer, A. Bauer, O.M. Böhm, A. Limberg, M. Cordes, Chem. Eur. J. 1999, 5, 2483;
20. f) D. Schinzer, A. Bauer, J. Schieber, Chem. Eur. J. 1999, 5, 2492;
21. g) J.D. White, R.G. Carter, K.F. Sundermann, J. Org. Chem. 1999, 64, 684;
22. h) M. Kalesse, M. Quitschalle, E. Claus, K. Gerlach, A. Pahl, H. H. Meyer, Eur. J. Org. Chem. 1999, 2817;
23. D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 10521;
24. j) B. Zhu, J. S. Panek, Org. Lett. 2000,2, 2575;
25. k) J. Mulzer, G. Karig, P. Pojarliev, Tetrahedron Lett. 2000, 41, 7635, and references therein.
26. For biological studies, see: a) refs. [1a] and [2]; b) P. F. Muhlradt, F. Sasse, Cancer Res. 1997, 57, 3344;
27. A. Wolff, A. Technau, G. Brandner, Int. J. Oncol. 1997, 11, 123;
28. R.J. Kowalski, P. Giannakakou, E. Hamel, J. Biol. Chem. 1997, 272, 2534;
29. e) T.-C. Chou, X.-G. Zhang, C. R. Harris, S. D. Kuduk, A. Balog, K. A. Savin, J. R. Bertino, S.J. Danishefsky, Proc. Natl. Acad. Sci. USA 1998, 95, 15798, and references therein.
30. For semisynthetic epothilones E (5) and F (6), see: G. Höfle, N. Glaser, M. Kiffe, H.-J. Hecht, F. Sasse, H. Reichenbach, Angew. Chem. 1999, 111, 2090;
31. Angew. Chem. Int. Ed. 1999, 38, 1971.
32. For the synthesis of desoxyepothilone F, see: C. B. Lee, T.-C. Chou, X.-G. Zhang, Z.G. Wang, S.D. Kuduk, M.D. Chappell, S.J. Stachel, S.J. Danishefsky, J. Org. Chem. 2000, 65, 6525.
33. For the synthesis of epothilones E (6) and F (6), see: a) K. C. Nicolaou, Y. He, F. Roschangar, N. P. King, D. Vourloumis, T. Li, Angew. Chem. 1998, 110, 89;
34. Angew. Chem. Int. Ed. 1998, 37, 84;
35. b) K. C. Nicolaou, N. P. King, M. R. V. Finlay, Y. He, F. Roschangar, D. Vourloumis, H. Vallberg, F. Sarabia, S. Ninkovic, D. Hepworth, Bioorg. Med. Chem. 1999, 7, 665;
36. K. C. Nicolaou, D. Hepworth, N. P. King, M. R. V. Finlay, R. Scarpelli, M. Pereira, A. Manuela, S. Bollbuck, A. Bigot, B. Werschkun, N. Winssinger, Chem. Eur. J. 2000, 6, 2783.
37. a) S. C. Sinha, C. F. Barbas III, R. A. Lerner, Proc. Natl. Acad. Sci. USA 1998, 95, 14603;
38. b) S.C. Sinha, J. Sun, G. Miller, C. F. Barbas III, R. A. Lerner, Org. Lett. 1999, 1, 1623;
39. S. C. Sinha, J. Sun, M. Wartmann, R. A. Lerner, Chem. Eur. J. 2001, 7, 1691.