An approach to epothilones based on olefin metathesis

Angewandte Chemie (International Edition in English)

Volumn 35, Issue 20, 1996, Pages 2399-2401

  Nicolaou, K C ^a,b   He, Yun ^a,b   Vourloumis, Dionisios ^a,b   Vallberg, Hans ^a,b   Yang, Zhen ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cyclizations; Epothilones; Natural products; Olefin metathesis; Synthetic methods

Indexed keywords

EID: 0030445213     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199623991     Document Type: Article

References (16)

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7. 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. Schwab, R. H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 25, 446-452, and references therein.
8. 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. Schwab, R. H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 25, 446-452, and references therein.
9. 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. Schwab, R. H. Grubbs, J. W. Ziller, ibid. 1996, 118, 100-110; c) R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 25, 446-452, and references therein.
10. Applications of the olefin metathesis reaction in medium and large ring synthesis, see a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) S. F. Martin, H.-J. Chen. A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; c) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; d) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; e) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194.
11. Applications of the olefin metathesis reaction in medium and large ring synthesis, see a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) S. F. Martin, H.-J. Chen. A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; c) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; d) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; e) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194.
12. Applications of the olefin metathesis reaction in medium and large ring synthesis, see a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) S. F. Martin, H.-J. Chen. A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; c) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; d) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; e) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194.
13. Applications of the olefin metathesis reaction in medium and large ring synthesis, see a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) S. F. Martin, H.-J. Chen. A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; c) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; d) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; e) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194.
14. Applications of the olefin metathesis reaction in medium and large ring synthesis, see a) A. Fürstner, K. Langemann, J. Org. Chem. 1996, 61, 3942-3943; b) S. F. Martin, H.-J. Chen. A. K. Courtney, Y. Liao, M. Pätzel, M. N. Ramser, A. S. Wagman, Tetrahedron 1996, 52, 7251-7264; c) T. D. Clark, M. R. Ghadiri, J. Am. Chem. Soc. 1995, 117, 12364-12365; d) A. F. Houri, Z. Xu, D. A. Cogan, A. H. Hoveyda, ibid. 1995, 117, 2943-2944; e) B. C. Borer, S. Deerenberg, H. Bieräugel, U. K. Pandit, Tetrahedron Lett. 1994, 35, 3191-3194.
15. Compound 9 was synthesized from geraniol by standard chemistry: D. F. Taber, K. K. You, J. Am. Chem. Soc. 1995, 117, 5757-5762, and references therein. Both enantiomers of 6 may also be reached by asymmetric synthesis with chiral auxiliaries.
16. Ketoaldehyde 11 was prepared from propionyl chloride according to a published procedure: T. Inukai, R. Yoshizawa, J. Org. Chem. 1967, 32, 404-407.