The olefin metathesis approach to epothilone A and its analogues

Journal of the American Chemical Society

Volumn 119, Issue 34, 1997, Pages 7960-7973

  Nicolaou, K C ^a   He, Y ^a   Vourloumis, D ^a   Vallberg, H ^a   Roschangar, F ^a   Sarabia, F ^a   Ninkovic, S ^a   Yang, Z ^a   Trujillo, J I ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; EPOTHILONE A; EPOTHILONE A DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030755282     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971109i     Document Type: Article

References (46)

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31. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (c) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. (f) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
32. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (c) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. (f) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
33. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (c) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. (f) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
34. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (c) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. (f) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
35. For a number of applications of the olefin metathesis reaction in medium and large ring synthesis, see: (a) Borer, B. C.; Deerenberg, S.; Bieräugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365. (c) Houri, A. F.; Xu, Z.; Cogan, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944. (d) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943. (e) Martin, S. F.; Chen, H.-J.; Courtney, A. K.; Liao, Y.; Pätzel, M.; Ramser, M. N.; Wagman, A. S. Tetrahedron 1996, 52, 7251-7264. (f) Xu, Z.; Johannes, C. W.; Salman, S. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 10926-10927.
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46. We thank Dr. G. Höfle for a sample of natural epothilone A (1).