Total Synthesis of Epothilone E and Analogues with Modified Side Chains through the Stille Coupling Reaction

Angewandte Chemie - International Edition

Volumn 37, Issue 1-2, 1998, Pages 84-87

  Nicolaou, K C ^a   He, Yun ^a   Roschangar, Frank ^a   Paul King, N ^a   Vourloumis, Dionisios ^a   Li, Tianhu ^b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Epothilones; Natural products Stille coupling; Total synthesis

Indexed keywords

EID: 0031881549     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3773(19980202)37:1/2<84::aid-anie84>3.0.co;2-v     Document Type: Article

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37. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. in Organomet. Chem. 1977, 16, 283-317.
38. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. in Organomet. Chem. 1977, 16, 283-317.
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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. in Organomet. Chem. 1977, 16, 283-317.
40. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. 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; R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452, and references therein ; J. Tsuji, S. Hashiguchi, Tetrahedron Lett. 1980, 27, 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, Adv. in Organomet. Chem. 1977, 16, 283-317.
45. For a number of applications of the olefin metathesis reaction in the synthesis of medium and large rings, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 55, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; A. Fürstner, K. Langemann, J. Org. Chem. 1996, 67, 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.
46. For a number of applications of the olefin metathesis reaction in the synthesis of medium and large rings, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 55, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; A. Fürstner, K. Langemann, J. Org. Chem. 1996, 67, 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.
47. For a number of applications of the olefin metathesis reaction in the synthesis of medium and large rings, see: a) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 55, 3191-3194; b) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; A. Fürstner, K. Langemann, J. Org. Chem. 1996, 67, 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.
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