The 12,13-diol cyclization approach for a truly stereocontrolled total synthesis of epothilone B and the synthesis of a conformationally restrained analogue

Chemistry - A European Journal

Volumn 7, Issue 10, 2001, Pages 2261-2271

  Martin, Harry J ^a   Pojarliev, Peter ^a   Kählig, Hanspeter ^a   Mulzer, Johann ^a  

^a INSTITUT FÜR ORGANISCHE CHEMIE   (Austria)

Author keywords

Carbonyl addition; Epothilones; Epoxidations; Stereoselective synthesis; Total synthesis

Indexed keywords

ALDEHYDES; CARBON; CONFORMATIONS; CRYSTAL STRUCTURE; KETONES;

CYCLIZATION APPROACH;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; CITRONELLOL; EPOTHILONE B; EPOTHILONE DERIVATIVE; LACTIC ACID; MACROLIDE;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; EPOTHILONES; MACROLIDES; STEREOISOMERISM;

EID: 0035906802     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3765(20010518)7:10<2261::AID-CHEM2261>3.0.CO;2-F     Document Type: Article

References (63)

1. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671;
2. Angew. Chem. Int. Ed. Engl. 1996, 35, 1567.
3. 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;
4. b) reviews of the chemistry and biology of the epothilones, see K. C. Nicolaou, F. Roschangar, D. Vourloumis, Angew. Chem. 1998, 110, 2120;
5. Angew. Chem. Int. Ed. 1998, 37, 2014;
6. J. Mulzer, Chem. Mon. 2000, 131, 205.
7. Syntheses of epothilone B: a) D.-S. Su, D. Meng, P. Bertinato, A. Balog, E. J. Sorensen, S. J. Danishefsky, Y. H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Angew. Chem. 1997, 109, 775;
8. Angew. Chem. Int. Ed. Engl. 1997, 36, 757;
9. b) 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;
10. c) D. Meng, P. Bertinato, A. Balog, D.-S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10073;
11. d) S. A. May, P. A. Grieco, Chem. Commun. 1998, 1597;
12. e) D. Schinzer, A. Bauer, J. Schieber, Synlett 1998, 861;
13. f) A. Ballog, C. Harris, K. Savin, X.-G. Zhang, T.-C. Chou, S. J. Danishefsky, Angew. Chem. 1998, 110, 2821;
14. Angew. Chem. Int. Ed. 1998, 37, 2675;
15. g) J. Mulzer, A. Mantoulidis, E. Öhler, Tetrahedron Lett. 1998, 39, 8633;
16. h) J. D. White, R. G. Carter, K. F. Sundermann, J. Org. Chem. 1999, 64, 684;
17. i) James D. White, K. F. Sundermann, R. G. Carter, Org. Lett. 1999, 1, 1431;
18. j) H. J. Martin, M. Drescher, J. Mulzer, Angew. Chem. 2000, 112, 591;
19. Angew. Chem. Int. Ed. 2000, 39, 581;
20. k) J. Mulzer, A. Mantoulidis, E. Öhler, J. Org. Chem. 2000, 65, 7456;
21. l) D. Sawada, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2000, 122, 10521;
22. m) J. Mulzer, G. Karig P. Pojarliev, Tetrahedron Lett. 2000, 41, 7635
23. Syntheses of cpothilone analogues: a) see ref. [2b];
24. b) R. M. Borzilleri, X. Zheng, R. J. Schmidt, J. A. Johnson, S.-H. Kim, J. D. DiMarco, C. R. Fairchild, J. Z. Gougoutas, F. Y. F. Lee, B. H. Long, G. D. Vite, J. Am. Chem. Soc. 2000, 122, 8890;
25. c) S. J. Stachel, M. D. Chappell, C. B. Lee, S. J. Danishefsky, T.-C. Chou, L. He, S. B. Horwitz, Org. Lett. 2000, 2, 1637;
26. d) J. Johnson, S.-H. Kim, M. Bifano, J. DiMarco, C. Fairchild, J. Gougoutas, F. Lee, B. Long, J. Tokarski, G. Vite, Org. Lett. 2000, 2, 1537;
27. e) K. C. Nicolaou, D. Hepworth, N. P. King, M. R. V. Finlay, R. Scarpelli, M. M. A. Pereira, B. Bollbuck, A. Bigot, B. Werschkun, N. Winssinger, Chem. Eur. J. 2000, 6, 2783;
28. f) D. Schinzer, K.-H. Altmann, F. Stuhlmann, A. Bauer, M. Wartmann, ChemBio-Chem 2000, 1, 67;
29. g) K. C. Nicolaou, Y. He, F. Roschangar, N. P. King, D. Vourloumis, T. Li, Angew. Chem. 1998, 110, 89;
30. Angew. Chem. Int. Ed. 1998, 37, 84
31. h) K. C. Nicolaou, F. Sarabia, S. Ninkovic, M. R. V. Finlay, C. N. C. Boddy, Angew. Chem. 1998, 110, 85;
32. Angew. Chem. Int. Ed. 1998, 37, 81;
33. i) K. C. Nicolaou, H. Vallberg, N. P. King, F. Roschangar, Y. He, D. Vourloumis, C. G. Nicolaou, Chem. Eur. J. 1997, 3, 1957;
34. j) K. C. Nicolaou, F. Sarabia, M. R. V. Finlay, S. Ninkovic, N. P. King, D. Vourloumis, Y. He, Chem. Eur. J. 1997, 3, 1971;
35. k) K. C. Nicolaou, D. Vourloumis, T. Li, J. Pastor, N. Winssinger, Y. He, S. Ninkovic, F. Sarabia, H. Vallberg, F. Roschangar, N. P. King, M. R. V. Finlay, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. 1997, 109, 2181;
36. Angew. Chem. Int. Ed. Engl. 1997, 36, 2097;
37. l) J. D. Winkler, J. M. Holland, J. Kasparec, P. H. Axelsen, Tetrahedron 1999, 55, 8199;
38. m) K. C. Nicolaou, M. Ray, V. Finlay, S. Ninkovic, F. Sarabia, Tetrahedron 1998, 54, 7127;
39. n) K. C. Nicolaou, M. Ray, V. Finlay, S. Ninkovic, Y. He, Z. Yang, T. Li, F. Sarabia, D. Vourloumis, Chem. Biol. 1998, 5, 365.
40. a) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolaou, Angew. Chem. 1997, 109, 170;
41. Angew. Chem. Int. Ed. Engl. 1997, 36, 166;
42. b) D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543;
43. Angew. Chem. Int. Ed. Engl. 1997, 36, 523;
44. c) D. Schinzer, A. Bauer, O. M. Böhm, A. Limberg, M. Cordes, Chem. Eur. J. 1999, 5, 2483;
45. d) 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;
46. e) D. Meng, P. Bertinato, A. Balog, D. S. Su, T. Kamenecka, E. J. Sorensen, S. J. Danishefsky, J. Am. Chem. Soc. 1997, 119, 10073.
47. A. Balog, D. Meng, P. Kamenecka, T. Bertinato, D. S. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976;
48. Angew. Chem. Int. Ed. Engl. 1996, 35, 2801.
49. D. Sawada, M. Shibasaki, Angew. Chem. 2000, 112, 215;
50. Angew. Chem. Int. Ed. 2000, 39, 209.
51. S. C. Sinha, C. F. Barbas III, R. A. Lerner, Proc. Natl. Acad. Sci. USA 1998, 39, 8633.
52. Review: R. M. Devant, H.-E. Radunz, Houben Weyl, Methods of Organic Chemistry, Vol. E21b: Stereoselective Synthesis (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart, 1995, p. 1151.
53. H. Kühne, "Konformationskontrolle durch cyclische Ketale bei Carbonyladditionen metallorganischer Reagenzien", Diploma Thesis, Freie Universität Berlin, 1992.
54. K. Gerlach, M. Quitschalle, M. Kalesse, Tetrahedron Lett. 1999, 40, 3553.
55. a) J. Mulzer, H. M. Kirstein, J. Buschmann, C. Lehmann, P. Luger, J. Am. Chem. Soc. 1991, 113, 910;
56. b) N. K. Kochetkov, A. F. Sviridov, M. S. Ermolenko, D. V. Vashunsky, V. S. Borodkin, Tetrahedron Lett. 1987, 28, 235;
57. c) N. K. Kochetkov, A. F. Sviridov, M. S. Ermolenko, D. V. Vashunsky, V. S. Borodkin, Tetrahedron 1989, 45, 5109;
58. d) G. Stork, I. Patterson, F. K. C. Lee, J. Am. Chem. Soc. 1982, 104, 4686.
59. L. A. Paquette, D. G. Maynard, J. Am. Chem. Soc. 1992, 114, 5018.
60. R. O. Duthaler, A. Hafner, Chem. Rev. 1992, 92, 807.
61. B. S. Bal, W. E. Childers Jr., H. W. Pinnick, Tetrahedron 1981, 37, 2091.
62. I. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989.
63. R. E. Taylor, J. Zajicek, J. Org. Chem. 1999, 64, 7224.