Stereoselective synthesis of 12,13-cyclopropyl-epothilone B and side-chain-modified variants

Organic Letters

Volumn 13, Issue 6, 2011, Pages 1436-1439

  Schiess, Raphael ^a   Gertsch, Jürg ^b   Schweizer, W Bernd ^a   Altmann, Karl Heinz ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF BERN   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; EPOTHILONE B; EPOTHILONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CYCLOPROPANES; EPOTHILONES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79952583833     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200114k     Document Type: Article

References (38)

1. Altmann, K.-H.; Pfeiffer, B.; Arseniyadis, S.; Pratt, B. A.; Nicolaou, K. C. ChemMedChem 2007, 2, 396
2. Höfle, G.; Reichenbach, H. Epothilone, a myxobacterial metabolite with promising antitumor activity. In Anticancer Agents from Natural Products; Cragg, G. M.; Kingston, D. G. I.; Newman, D. G., Ed.; Taylor & Francis: Boca Raton, FL, 2005; pp 413.
3. For a review, see: Coley, H. M. Cancer Treat. Rev. 2008, 34, 378
4. http://www.cancer.gov/cancertopics/druginfo/fda-ixabepilone
5. Johnson, J.; Kim, S. H.; Bifano, M.; DiMarco, J.; Fairchild, C.; Gougoutas, J.; Lee, F.; Long, B.; Tokarski, J.; Vite, G. Org. Lett. 2000, 2, 1537
6. Xu, X.; Zeng, J.; Mylott, W.; Arnold, M.; Waltrip, J.; Iacono, L.; Mariannino, T.; Stouffer, B. J. Chromatogr. B 2010, 878, 525
7. Cömezoǧlu, S. N.; Ly, Van T.; Zhang, D.; Humphreys, W. G.; Bonacorsi, S. J.; Everett, D. W.; Cohen, M. B.; Gan, J.; Beumer, J. H.; Beunen, J. H.; Schellens, J. H. M.; Lappin, G. Drug Metab. Pharmacokinet. 2009, 24, 511
8. Blum, W.; Aichholz, R.; Ramstein, P.; Kühnöl, J.; Brüggen, J.; O'Reilly, T.; Flörsheimer, A. Rapid Commun. Mass Spectrom. 2001, 15, 41
9. For a recent review on ADCs, see: Senter, P. Curr. Opin. Chem. Biol. 2009, 13, 235
10. Heterocycles were selected based on previous SAR data on other types of potent side-chain-modified epothilones (1) and the availability of the corresponding epoxides for biological comparison (for 16e and d).
11. Nicolaou, K. C.; Namoto, K.; Ritzén, A.; Ulven, T.; Shoji, M.; Li, J.; D'Amico, G.; Liotta, D.; French, C. T.; Wartmann, M.; Altmann, K.-H.; Giannakakou, P. J. Am. Chem. Soc. 2001, 123, 9313
12. Nicolaou, K. C.; Ritzén, A.; Namoto, K.; Buey, R. M.; Díaz, J. F.; Andreu, J. M.; Wartmann, M.; Altmann, K.-H.; O'Brate, A.; Giannakakou, P. Tetrahedron 2002, 58, 6413
13. Nicolaou, K. C.; Sasmal, P. K.; Rassias, G.; Reddy, M. V.; Altmann, K.-H.; Wartmann, M.; O'Brate, A.; Giannakakou, P. Angew. Chem., Int. Ed. 2003, 42, 3515
14. Based on literature data for two examples 12,13- trans configured CP epothilones of type B (methyl group on C12) appear to be significanly less active than the corresponding cis derivatives. (10, 11)
15. Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Chou, T.-C.; Dong, H. J.; Danishefsky, S. J. J. Am. Chem. Soc. 2004, 126, 10913
16. Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Chou, T.-C.; Dong, H. J.; Tong, W. P.; Danishefsky, S. J. J. Am. Chem. Soc. 2003, 125, 2899
17. Chou, T.-C.; Dong, H. J.; Rivkin, A.; Yoshimura, F.; Gabarda, A. E.; Cho, Y. S.; Tong, W. P.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2003, 42, 4761
18. Hindupur, R. M.; Panicker, B.; Valluri, M.; Avery, M. A. Tetrahedron Lett. 2001, 42, 7341
19. Sefkow, M.; Kiffe, M.; Schummer, D.; Höfle, G. Bioorg. Med. Chem. Lett. 1998, 8, 3025
20. The preparation of side-chain-modified analogs of 9,10-dehydro-Epo D from the corresponding ketone has been disclosed in a PCT patent application (WO2004043954 (A2)), without any comments on the stereochemical outcome of the Wittig reactions.
21. Feyen, F.; Jantsch, A.; Hauenstein, K.; Pfeiffer, B.; Altmann, K.-H. Tetrahedron 2008, 64, 7920
22. Seifert, A.; Vomund, S.; Grohmann, K.; Kriening, S.; Urlacher, V. K.; Laschat, S.; Pleiss, J. ChemBioChem 2009, 10, 853
23. Denmark, S. E.; Yang, S.-M. J. Am. Chem. Soc. 2002, 124, 15196
24. Mulzer, J.; Mantoulidis, A.; Oehler, E. J. Org. Chem. 2000, 65, 7456
25. White, J. D.; Hrnciar, P. J. Org. Chem. 2000, 65, 9129
26. Green, D. L. C.; Kiddle, J. J.; Thompson, C. M. Tetrahedron 1995, 51, 2865
27. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405
28. Phosphonate 5 is accessible from commerically available ethylphosphonic dichloride in a two-step sequence (cf. ref 19).
29. Charette, A. B.; Juteau, H.; Lebel, H.; Molinaro, C. J. Am. Chem. Soc. 1998, 120, 11943
30. He, R.; Deng, M. Z. Tetrahedron 2002, 58, 7613
31. The structure has been deposited in the Cambridge Crystallographic Data Base (deposition number CCDC 808039).
32. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485
33. Sharpless, K. B.; Young, M. W. J. Org. Chem. 1975, 40, 947
34. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989
35. Sen, S. E.; Roach, S. L.; Boggs, J. K.; Ewing, G. J.; Margrath, J. J. Org. Chem. 1997, 62, 6684
36. For experimental details see: Dietrich, S. A.; Lindauer, R.; Stierlin, C.; Gertsch, J.; Matesanz, R.; Notararigo, S.; Díaz, J. F.; Altmann, K.-H. Chem.-Eur. J. 2009, 15, 10144
37. These compounds were kindly provided by the Novartis Institute for Biomedical Research in Basel, Switzerland.
38. Chou, T.-C.; Zhang, X.; Zhong, Z.-Y.; Li, Y.; Feng, L.; Eng, S.; Myles, D. M.; Johnson, R., Jr.; Wu, N.; Yin, Y. I.; Wilson, R. M.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 13157