Total synthesis of the tubulin inhibitor WF-1360f based on macrocycle formation through ring-closing alkyne metathesis

Angewandte Chemie - International Edition

Volumn 52, Issue 22, 2013, Pages 5866-5870

  Neuhaus, Christian M ^a   Liniger, Marc ^a   Stieger, Martin ^b   Altmann, Karl Heinz ^a  

^a ETH ZURICH   (Switzerland)

^b BASILEA PHARMACEUTICA INTERNATIONAL LTD   (Switzerland)

Author keywords

drug discovery; metathesis; natural products; rhizoxin; total synthesis

Indexed keywords

DRUG DISCOVERY; METATHESIS; NATURAL PRODUCTS; RHIZOXIN; TOTAL SYNTHESIS;

HYDROCARBONS;

SYNTHESIS (CHEMICAL);

ALKYNE; MACROCYCLIC COMPOUND; MACROLIDE; RHIZOXIN; TUBULIN MODULATOR; VINYL DERIVATIVE; VINYL IODIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKYNES; MACROCYCLIC COMPOUNDS; MACROLIDES; MOLECULAR STRUCTURE; TUBULIN MODULATORS; VINYL COMPOUNDS;

EID: 84878083572     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300576     Document Type: Article

References (48)

1. S. Iwasaki, H. Kobayashi, J. Furukawa, M. Namikoshi, S. Okuda, Z. Sato, I. Matsuda, T. Noda, J. Antibiot. 1984, 37, 354-362.
2. Elucidation of the absolute configuration of 1:, S. Iwasaki, M. Namikoshi, H. Kobayashi, J. Furukawa, S. Okuda, A. Itai, A. Kasuya, Y. Iitaka, Z. Sato, J. Antibiot. 1986, 39, 424-429.
3. L. P. Partida-Martinez, C. Hertweck, Nature 2005, 437, 884-888.
4. M. Takahashi, S. Iwasaki, H. Kobayashi, S. Okuda, T. Murai, Y. Sato, T. Haraguchi-Hiraoka, H. Nagano, J. Antibiot. 1987, 40, 66-72.
5. S. Kiyoto, Y. Kawai, T. Kawakita, E. Kino, M. Okuhara, I. Uchida, H. Tanaka, M. Hashimoto, H. Terano, M. Kohsaka, H. Aoki, H. Imanaka, J. Antibiot. 1986, 39, 762-772
6. T. Tsuruo, T. Ohhara, H. Iida, S. Tsukagoshi, Z. Sato, I. Matsuda, S. Iwasaki, S. Okuda, F. Shimizu, K. Sasagawa, M. Fukami, K. Fukuda, M. Arakawa, Cancer Res. 1986, 46, 381-385.
7. H. L. McLeod, L. S. Murray, J. Wanders, A. Setanoians, M. A. Graham, N. Pavlidis, B. Heinrich, W. W. TenBokkelHuinink, D. J. Wagener, S. Aamdal, J. Verweij, Br. J. Cancer 1996, 74, 1944-1948
8. A. R. Hanauske, G. Catimel, S. Aamdal, W. TenBokkelHuinink, R. Paridaens, N. Pavlidis, S. B. Kaye, A. Te Velde, J. Wanders, J. Verweij, Br. J. Cancer 1996, 73, 397-399.
9. S. Iwasaki, M. Namikoshi, H. Kobayashi, J. Furukawa, S. Okuda, Chem. Pharm. Bull. 1986, 34, 1387-1390.
10. K. Scherlach, L. P. Partida-Martinez, H.-M. Dahse, C. Hertweck, J. Am. Chem. Soc. 2006, 128, 11529-11536.
11. For a review see:, J. Hong, J. D. White, Tetrahedron 2004, 60, 5653-5681.
12. M. Nakada, S. Kobayashi, S. Iwasaki, M. Ohno, Tetrahedron Lett. 1993, 34, 1039-1042.
13. For a general review on the metathesis reaction see:, A. H. Hoveyda, A. R. Zhugralin, Nature 2007, 450, 243-251.
14. For a general review see:, A. Fürstner, P. W. Davies, Chem. Commun. 2005, 2307-2320.
15. J. Heppekausen, R. Stade, A. Kondoh, G. Seidel, R. Goddard, A. Fürstner, Chem. Eur. J. 2012, 18, 10281-10299
16. J. Heppekausen, R. Stade, R. Goddard, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 11045-11057.
17. J. Willwacher, N. Kausch-Busies, A. Fürstner, Angew. Chem. 2012, 124, 12207-12212
18. Angew. Chem. Int. Ed. 2012, 51, 12041-12046
19. W. Chaładaj, M. Corbet, A. Fürstner, Angew. Chem. 2012, 124, 7035-7039
20. Angew. Chem. Int. Ed. 2012, 51, 6929-6933
21. V. Hickmann, A. Kondoh, B. Gabor, M. Alcazaro, A. Fürstner, J. Am. Chem. Soc. 2011, 133, 13471-13480
22. K. Lehr, R. Mariz, L. Leseurre, B. Gabor, A. Fürstner, Angew. Chem. 2011, 123, 11575-11579
23. Angew. Chem. Int. Ed. 2011, 50, 11373-11377
24. K. Micoine, A. Fürstner, J. Am. Chem. Soc. 2010, 132, 14064-14066.
25. I. Paterson, J. M. Goodman, M. A. Lister, R. C. Schumann, C. K. McClure, M. D. Norcross, Tetrahedron 1990, 46, 4663-4684.
26. M. Handa, K. A. Scheidt, M. Bossart, N. Zheng, W. R. Roush, J. Org. Chem. 2008, 73, 1031-1035.
27. J. D. White, P. R. Blakemore, N. J. Green, E. B. Hauser, M. A. Holoboski, L. E. Keown, C. S. NylundKolz, B. W. Phillips, J. Org. Chem. 2002, 67, 7750-7760.
28. D. A. Evans, K. T. Chapman, E. M. Carreira, J. Am. Chem. Soc. 1988, 110, 3560-3578.
29. M. T. Crimmins, A. C. DeBaillie, J. Am. Chem. Soc. 2006, 128, 4936-4937.
30. S. Takano, K. Inomata, K. Samizu, S. Tomita, M. Yanase, M. Suzuki, Y. Iwabuchi, T. Sugihara, K. Ogasawara, Chem. Lett. 1989, 1283-1284.
31. Y. Naruta, Y. Nishigaichi, K. Maruyama, Chem. Lett. 1986, 1857-1860.
32. E. J. Corey, C.-M. Yu, S. S. Kim, J. Am. Chem. Soc. 1989, 111, 5495-5496.
33. D. R. Williams, K. G. Meyer, K. Shamim, S. Patnaik, Can. J. Chem. 2004, 82, 120-130.
34. The absolute configuration of alcohol 23 was secured by Mosher ester analysis:, T. R. Hoye, C. S. Jeffrey, F. Shao, Nat. Protoc. 2007, 2, 2451-2458.
35. J. A. Lafontaine, D. P. Provencal, C. Gardelli, J. W. Leahy, J. Org. Chem. 2003, 68, 4215-4234.
36. J. Li, D. Menche, Synthesis 2009, 1904-1908.
37. 3 system:, J.-M. Vatèle, Synlett 2006, 2055-2058.
38. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett. 1984, 25, 2183-2186.
39. B. M. Trost, Z. T. Ball, J. Am. Chem. Soc. 2005, 127, 17644-17655.
40. F. Lacombe, K. Radkowski, G. Seidel, A. Fürstner, Tetrahedron 2004, 60, 7315-7324.
41. So far EPHP has been employed only in the radical deoxygenation of alcohols and vicinal diols:, O. Jang, D. H. Cho, Tetrahedron Lett. 2002, 43, 5921-5924.
42. 2O.
43. A new method for the conversion of alkynes into E olefins has recently been reported by the Fürstner group. Unfortunately, 1,3-enyne units could not be hydrogenated by this method:, K. Radkowski, B. Sundararaju, A. Fürstner, Angew. Chem. 2013, 125, 373-378
44. Angew. Chem. Int. Ed. 2013, 52, 355-360.
45. A. S. Kende, B. E. Blass, J. R. Henry, Tetrahedron Lett. 1995, 36, 4741-4744.
46. The stability of rhizoxin (1) has been investigated:, V. J. Stella, K. Umprayn, W. N. Waugh, Int. J. Pharm. 1988, 43, 191-199.
47. K. B. Sharpless, R. C. Michaelson, J. Am. Chem. Soc. 1973, 95, 6136-6137.
48. See also:, Y. Kato, Y. Ogawa, T. Imada, S. Iwasaki, N. Shimazaki, T. Kobayashi, T. Komai, J. Antibiot. 1991, 44, 66-75.