Total synthesis of oxazole- and cyclopropane-containing epothilone A analogues by the olefin metathesis approach

Chemistry - A European Journal

Volumn 3, Issue 12, 1997, Pages 1957-1970

  Nicolaou, K C ^a   Vallberg, Hans ^a   King, N Paul ^a   Roschangar, Frank ^a   He, Yun ^a   Vourloumis, Dionisios ^a   Nicolaou, Christopher G ^a  

^a NONE

Author keywords

Cycloprones; Epothilone; Metathesis; Oxazoles; Total synthesis

Indexed keywords

EID: 0031460524     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970031211     Document Type: Article

References (60)

1. a) G. Höfle, N. Bedorf, K. Gerth, H. Reichenbach (GBF), DE-4138042, 1993 (Chem. Abstr. 1993, 120, 52841);
2. b) K. Gerth, N. Bedorf, G. Höfle, H. Irschik, H. Reichenbach, J. Antibiot. 1996, 49, 560-563.
3. 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, 2325-2333.
4. R. J. Kowalski, P. Giannakakou, E. Hamel, J. Biol. Chem. 1997, 272, 2534-2541.
5. S. B. Horwitz, J. Fant, P. B. Schiff, Nature 1979, 277, 665-667.
6. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569.
7. G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth, H. Reichenbach, Angew. Chem. 1996, 108, 1671-1673; Angew. Chem. Int. Ed. Engl. 1996, 35, 1567-1569.
8. a) K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, Z. Yang, Angew. Chem. 1996, 108, 2554-2556; Angew. Chem. Int. Ed. Engl. 1996, 35, 2399-2401;
9. a) K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, Z. Yang, Angew. Chem. 1996, 108, 2554-2556; Angew. Chem. Int. Ed. Engl. 1996, 35, 2399-2401;
10. b) D. Meng, E. J. Sorensen, P. Bertinato, S. J. Danishefsky, J. Org. Chem. 1996, 61, 7998-7999;
11. c) P. Bertinato, E. J. Sorensen, D. Meng, S. J. Danishefsky, ibid. 1996, 61, 8000-8001;
12. d) D. Schinzer, A. Limberg, O. M. Böhm, Chem. Eur. J. 1996, 2, 1477-1482;
13. e) J. Mulzer, A. Mantoulidis, Tetrahedron Lett. 1996, 37, 9179-9182;
14. f) E. Claus, A. Pahl, P. G. Jones, H. M. Meyer, M. Kalesse, ibid. 1997, 38, 1359-1362;
15. g) T. Gabriel, L. Wessjohann, ibid. 1997, 38, 1363-1366;
16. h) R. E. Taylor, J. D. Haley, ibid. 1997, 38, 2061-2064.
17. a) A Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976-2978; Angew. Chem. Int. Ed. Engl. 1996, 35, 2801-2803;
18. a) A Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E. J. Sorensen, S. J. Danishefsky, Angew. Chem. 1996, 108, 2976-2978; Angew. Chem. Int. Ed. Engl. 1996, 35, 2801-2803;
19. b) D. Meng, D.-S. Su, A. Balog, P. Bertinato, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, J. Am. Chem. Soc. 1997, 119, 2733-2734.
20. a) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolaou, Angew. Chem. 1997, 109, 170-172; Angew. Chem. Int. Ed. Engl. 1997, 36, 166-168;
21. a) Z. Yang, Y. He, D. Vourloumis, H. Vallberg, K. C. Nicolaou, Angew. Chem. 1997, 109, 170-172; Angew. Chem. Int. Ed. Engl. 1997, 36, 166-168;
22. b) K. C. Nicolaou, F. Sarabia, S. Ninkovic, Z. Yang, ibid. 1997, 109, 539-540 and 1997, 36, 525-526.
23. b) K. C. Nicolaou, F. Sarabia, S. Ninkovic, Z. Yang, ibid. 1997, 109, 539-540 and 1997, 36, 525-526.
24. D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543-544; Angew. Chem. Int. Ed. Engl. 1997, 36, 523-524.
25. D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm, M. Cordes, Angew. Chem. 1997, 109, 543-544; Angew. Chem. Int. Ed. Engl. 1997, 36, 523-524.
26. K. C. Nicolaou, N. Winssinger, J. A. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou, E. Hamel, Nature 1997, 387, 268-272.
27. 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, 7960-7973.
28. 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, 775-777; Angew. Chem. Int. Ed. Engl. 1997, 36, 757-759.
29. 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, 775-777; Angew. Chem. Int. Ed. Engl. 1997, 36, 757-759.
30. 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, 7974-7991.
31. G. Höfle, personal communication.
32. A. Balog, P. Bertinato, D.-S. Su, D. Meng, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He, S. B. Horwitz, Tetrahedron Lett. 1997, 38, 4529-4532.
33. K. C. Nicolaou, F. Sarabia, M. R. V. Finlay, S. Ninkovic, N. P. King, D. Vourloumis, Y. He, Chem. Eur. J. 1997, 3, 1971.
34. A. S. Kende, B. E. Blass, J. R. Henry, Tetrahedron Lett. 1995, 36, 4741-4744.
35. U. S. Racherla, H. C. Brown, J. Org. Chem. 1991, 56, 401-404.
36. a) J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512-519;
37. b) T. Kusumi, I. Ohtani, Y. Inouye, H. Kakisawa, Tetrahedron Lett. 1988, 29, 4731-4734;
38. c) I. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092-4096.
39. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
40. b) For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
41. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
42. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
43. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
44. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
45. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
46. For the development of the olefin metathesis as a ring-forming reaction, see: a) W. J. Zuercher, M. Hashimoto, R. H. Grubbs, J. Am. Chem. Soc. 1996, 118, 6634-6640; b) P. R. Schwab, H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452 and references therein; d) J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 21, 2955-2959. For some earlier pioneering studies on this reaction, see: e) T. J. Katz, S. J. Lee, N. Acton, ibid. 1976, 4247-4250; f) T. J. Katz, N. Acton, ibid. 1976, 4241-4254; g) T. J. Katz, J. McGinnis, C. Altus, J. Am. Chem. Soc. 1976, 98, 606-608; h) T. J. Katz, Advances in Organomet. Chem. 1977, 16, 283-317.
47. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; c) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; d) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; e) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; f) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
48. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; c) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; d) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; e) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; f) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
49. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; c) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; d) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; e) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; f) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
50. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; c) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; d) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; e) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; f) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
51. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; c) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; d) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; e) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; f) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
52. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; c) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; d) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; e) S. F. Martin, H.-J. Chen, A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; f) Z. Xu, C. W. Johannes, S. S. Salman, A. H. Hoveyda, J. Am. Chem. Soc. 1996, 118, 10926-10927.
53. For other independent approaches to epothilones based on the olefin metathesis reaction, see refs. [6h], [7b], and [9].
54. N. K. Chaudhuri, T. J. Ball, J. Org. Chem. 1982, 47, 5196-5198.
55. The use of mCPBA or methyl(trifluoromethyl)dioxirane as employed for the epoxidation of the corresponding thiazoles proved inferior in this instance, leading to significant decomposition.
56. 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, T. Fojo, P. Giannakakou, P. Verdier-Pinard, E. Hamel, Angew. Chem. Int. Ed. Engl. 1997, 36, 2097-2103.
57. a) H. W. Pinnick, Y.-H. Chang, Tetrahedron Lett. 1979, 837-840;
58. b) D. A. White, Synth. Commun. 1977, 7, 559.
59. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem. 1981, 46, 3936-3938.
60. D. Yang, M.-K. Wong, Y.-C. Yip, J. Org. Chem. 1995, 60, 3887-3889.