Synthesis of a simplified analogue of eleutherobin via a Claisen rearrangement and ring closing metathesis strategy

Chemical Communications

Volumn , Issue 14, 2005, Pages 1860-1862

  Chiang, Gary C H ^a   Bond, Andrew D ^a   Ayscough, Andrew ^b   Pain, Gilles ^b   Ducki, Sylvie ^c   Holmes, Andrew B ^a,d  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b British Biotech Pharmaceuticals Ltd   (United Kingdom)

^c UNIVERSITY OF SALFORD   (United Kingdom)

^d UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

CYTOTOXIC AGENT; ELEUTHEROBIN; PACLITAXEL;

ARTICLE; CHEMICAL REACTION; CLAISEN CONDENSATION; EPOXIDATION; METHODOLOGY; METHYLATION; REACTION ANALYSIS; RING CLOSING METATHESIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THERMODYNAMICS;

EID: 17444408490     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b413426e     Document Type: Article

References (13)

1. T. Lindel, P. R. Jensen, W. Fenical, B. H. Long, A. M. Casazza, J. Carboni and C. R. Fairchild, J. Am Chem. Soc., 1997, 119, 8744.
2. B. H. Long, J. M. Carboni, A. J. Wasserman, L. A. Cornell, A. M. Casazza, P. R. Jensen, T. Lindel, W. Fenical and C. R. Fairchild, Cancer Res., 1998, 58, 1111.
3. K. C. Nicolaou, T. Ohshima, S. Hosokawa, F. L. van Delft, D. Vourlourais, J. Y. Xu, J. Pfefferkorn and S. Kim. J. Am. Chem. Soc., 1998, 120, 8674.
4. X. T. Chen, S. K. Bhattacharya, B. Zhou, C. E. Gutteridge, T. R. R. Pettus and S. J. Danishefsky, J. Am. Chem. Soc., 1999, 121, 6563.
5. M. S. Congreve, A. B. Holmes, A. B. Hughes and M. G. Looney, J. Am. Chem. Soc., 1993, 115, 5815.
6. J. E. P. Davidson, R. Gilmour, S. Ducki, J. E. Davies, R. Green, J. W. Burton and A. B. Holmes, Synlett, 2004, 1434.
7. K. C. Nicolaou, N. Winssinger, D. Vourloumis, T. Ohshima, S. Kim, J. Y. Xu and T. Li, J. Am Chem. Soc., 1998, 120, 10814.
8. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 1995, 34, 2039.
9. For other ring closing metathesis approaches to eunicellin analogues and the evaluation of their tubulin stabilising properties see: R. Beumer, P. Bayon, P. Bugada, S. Ducki, N. Mongelli, F. R. Sirtori, J. Telser and C. Gennari, Tetrahedron, 2003, 59, 8803 and references cited therein.
10. K. B. Sharpless, M. A. Umbreit, T. H. Nieh and T. C. Flood, J. Am. Chem. Soc., 1972, 94, 6538.
11. 12.§
12. G. M. Sheldrick, SHELXS-97/SHELXL-97, University of Göttingen, Germany, 1997.
13. Microtubules did not depolymerise at 10°C.