DOI: 10.1039/A705845D
(Paper)
Reference Section for: Chem. Commun., 1997, 2343-2344
Total synthesis of 26-hydroxyepothilone B and related analogues
(Note: The full text of this document is currently only available in the PDF Version )
K. C. Nicolaou, Sacha Ninkovic, M. Ray V. Finlay, Francisco Sarabia and Tianhu Li
Abstract
A series of 26-substituted epothilones B (3, 22, 23a–n and 24a–h,j–l,o) have been constructed by total synthesis involving a selective Wittig olefination, an aldol reaction and a macrolactonization as key steps.
References
- G. Höfle, N. Bedorf, H. Steinmetz, D. Schomburg, K. Gerth and H. Reichenbach, Angew. Chem., Int. Ed. Engl., 1996, 35, 1567 CrossRef.
- D. M. Bollag, P. A. McQueney, J. Zhu, O. Hensens, L. Koupal, J. Liesch, M. Goetz, E. Lazarides and C. M. Woods, Cancer Res., 1995, 55, 2325 CAS.
- R. J. Kowalski, P. Giannakakou and E. Hamel, J. Biol. Chem., 1997, 272, 2534 CrossRef CAS.
- S. B. Horwitz, J. Fant and P. B. Schiff, Nature, 1979, 277, 665 CAS.
- K. C. Nicolaou, N. Winssinger, J. A. Pastor, S. Ninkovic, F. Sarabia, Y. He, D. Vourloumis, Z. Yang, T. Li, P. Giannakakou and E. Hamel, Nature, 1997, 387, 268 CrossRef CAS.
- D.-S. Su, D. Meng, P. Bertinato, A. Balog, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He and S. B. Horwitz, Angew. Chem., Int. Ed. Engl., 1997, 36, 757 CrossRef CAS.
- K. C. Nicolaou, S. Ninkovic, F. Sarabia, D. Vourloumis, Y. He, H. Vallberg, M. R. V. Finlay and Z. Yang, J. Am. Chem. Soc., 1997, 119, 7974 CrossRef CAS.
- A. Balog, D. Meng, T. Kamenecka, P. Bertinato, D.-S. Su, E. J. Sorensen and S. J. Danishefsky, Angew. Chem., Int. Ed. Engl., 1996, 35, 2801 CrossRef CAS; D. Meng, D.-S. Su, A. Balog, P. Bertinato, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He and S. B. Horwitz, J. Am. Chem. Soc., 1997, 119, 2733 CrossRef CAS.
- Z. Yang, Y. He, D. Vourloumis, H. Vallberg and K. C. Nicolaou, Angew. Chem., Int. Ed. Engl., 1997, 36, 166 CrossRef CAS; K. C. Nicolaou, F. Sarabia, S. Ninkovic and Z. Yang, Angew. Chem., Int. Ed. Engl., 1997, 36, 525 CrossRef CAS.
- D. Schinzer, A. Limberg, A. Bauer, O. M. Böhm and M. Cordes, Angew. Chem., Int. Ed. Engl., 1997, 36, 523 CrossRef CAS.
- K. C. Nicolaou, Y. He, D. Vourloumis, H. Vallberg, F. Roschangar, F. Sarabia, S. Ninkovic, Z. Yang and J. I. Trujillo, J. Am. Chem. Soc., 1997, 119, 7960 CrossRef.
- Isolation and structure elucidation: G. Höfle, personal communication.
- K. C. Nicolaou, Y. He, F. Roschangar, N. P. King and D. Vourloumis, Angew. Chem., in the press Search PubMed.
- K. C. Nicolaou, H. Vallberg, N. P. King, F. Roschangar, Y. He, D. Vourloumis and C. G. Nicolaou, Chem. Eur. J., in the press Search PubMed.
- K. C. Nicolaou, F. Sarabia, M. R. V. Finlay, S. Ninkovic, N. P. King, D. Vourloumis and Y. He, Chem. Eur. J., in the press Search PubMed.
- A. Balog, P. Bertinato, D.-S. Su, D. Meng, E. J. Sorensen, S. J. Danishefsky, Y.-H. Zheng, T.-C. Chou, L. He and S. B. Horwitz, Tetrahedron Lett., 1997, 38, 4529 CrossRef CAS.
- 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 and E. Hamel, Angew. Chem., Int. Ed. Engl., 1997, 36, 2097 CrossRef CAS.
- D. Enders, A. Plant, D. Backhaus and U. Reinhold, Tetrahedron, 1995, 51, 10 699 CrossRef CAS.