Synthesis and biological activity of 7,8,9-trideoxy- and 7R DesTHP-peloruside A

Chemistry - A European Journal

Volumn 19, Issue 39, 2013, Pages 13105-13111

  Wullschleger, Christoph W ^a   Gertsch, Jürg ^b   Altmann, Karl Heinz ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITY OF BERN   (Switzerland)

Author keywords

natural products; peloruside A; structure activity relationships; total synthesis; tubulin

Indexed keywords

NATURAL PRODUCTS; PELORUSIDE A; STRUCTURE ACTIVITY RELATIONSHIPS; TOTAL SYNTHESIS; TUBULIN;

ALDEHYDES; CELL CULTURE; ISOMERS; STEREOCHEMISTRY; STEREOSELECTIVITY;

BIOACTIVITY;

EID: 84884530929     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201301796     Document Type: Article

References (53)

1. L. M. West, P. T. Northcote, C. N. Battershill, J. Org. Chem. 2000, 65, 445.
2. K. A. Hood, L. M. West, B. Rouwé, P. T. Northcote, M. V. Berridge, S. J. Wakefield, J. H. Miller, Cancer Res. 2002, 62, 3356.
3. T. N. Gaitanos, R. M. Buey, J. F. Díaz, P. T. Northcote, P. Teesdale-Spittle, J. M. Andreu, J. H. Miller, Cancer Res. 2004, 64, 5063.
4. K.-H. Altmann, J. Gertsch, Nat. Prod. Rep. 2007, 24, 327.
5. J. T. Huzil, J. K. Chik, G. W. Slysz, H. Freedman, J. Tuszynski, R. E. Taylor, D. L. Sackett, D. C. Schriemer, J. Mol. Biol. 2008, 378, 1016
6. A. Begaye, S. Trostel, Z. Zhao, R. E. Taylor, D. C. Schriemer, D. L. Sackett, Cell Cycle 2011, 10, 3387.
7. E. Hamel, B. W. Day, J. H. Miller, M. K. Jung, P. T. Northcote, A. K. Ghosh, D. P. Curran, M. Cushman, K. C. Nicolaou, I. Paterson, E. J. Sorensen, Mol. Pharmacol. 2006, 70, 1555.
8. A. Wilmes, K. Bargh, C. Kelly, P. T. Northcote, J. H. Miller, Mol. Pharm. 2007, 4, 269
9. A. Wilmes, D. O'Sullivan, A. Chan, C. Chandrahasen, I. Paterson, P. T. Northcote, A. C. LaFlamme, J. H. Miller, Cancer Chemother. Pharmacol. 2011, 68, 117.
10. X. Liao, Y. Wu, J. K. DeBrabander, Angew. Chem. 2003, 115, 1686
11. Angew. Chem. Int. Ed. 2003, 42, 1648 (ent- 1)
12. M. Jin, R. E. Taylor, Org. Lett. 2005, 7, 1303
13. A. K. Ghosh, X. Xu, J. H. Kim, C. X. Xu, Org. Lett. 2008, 10, 1001
14. A. B. Smith III, J. M. Cox, N. Furuichi, C. S. Kenesky, J. Zheng, O. Atasoylu, W. M. Wuest, Org. Lett. 2008, 10, 5501 (2-epi- 1)
15. D. A. Evans, D. S. Welch, A. W. Speed, G. A. Moniz, A. Reichelt, S. Ho, J. Am. Chem. Soc. 2009, 131, 3840
16. M. A. McGowan, C. P. Stevenson, M. A. Schiffler, E. N. Jacobsen, Angew. Chem. 2010, 122, 6283
17. Angew. Chem. Int. Ed. 2010, 49, 6147
18. T. R. Hoye, J. Jeon, L. C. Kopel, T. D. Ryba, M. A. Tennakoon, Y. Wang, Angew. Chem. 2010, 122, 6287
19. Angew. Chem. Int. Ed. 2010, 49, 6151.
20. For a synthesis of the related peloruside B see:, A. J. Singh, C. X. Xu, X. Xu, L. M. West, A. Wilmes, A. Chan, E. Hamel, J. H. Miller, P. T. Northcote, A. K. Ghosh, J. Org. Chem. 2010, 75, 2.
21. B. Pera, M. Razzak, C. Trigili, O. Pineda, A. Canales, R. M. Buey, J. Jimenez-Barbero, P. T. Northcote, I. Paterson, I. Barasoain, J. F. Díaz, ChemBioChem 2010, 11, 1669
22. A. J. Singh, M. Razzak, P. Teesdale-Spittle, T. N. Gaitanos, A. Wilmes, I. Paterson, J. M. Goodman, J. H. Miller, P. T. Northcote, Org. Biomol. Chem. 2011, 9, 4456
23. Z. Zhao, R. E. Taylor, Org. Lett. 2012, 14, 669
24. N. Zimmermann, P. Pinard, B. Carboni, P. Gosselin, C. Gaulon-Nourry, G. Dujardin, S. Collet, J. Lebreton, M. Mathé-Allainmat, Eur. J. Org. Chem. 2013, 2303.
25. C. W. Wullschleger, J. Gertsch, K.-H. Altmann, Org. Lett. 2010, 12, 1120.
26. B. Pfeiffer, unpublished results.
27. A. Hafner, R. O. Duthaler, R. Marti, G. Rihs, P. Rothe-Streit, F. Schwarzenbach, J. Am. Chem. Soc. 1992, 114, 2321.
28. S. D. Rychnovsky, D. J. Skalitzky, Tetrahedron Lett. 1990, 31, 945
29. C. F. Tormena, L. C. Dias, R. Rittner, J. Phys. Chem. A 2005, 109, 6077.
30. In ref.[11] we reported the addition of the vinyllithium species derived from 9 to an aldehyde related to 10 (or 22) to proceed with a d.r. of ca. 2:1. However, we have now established that this previous addition reaction was also completely selective and that what we had assumed to be the undesired diastereoisomer was in fact ketone 15. Ketone 15 has been described:, A. P. Duncan, J. L. Leighton, Org. Lett. 2004, 6, 4117.
31. E. J. Corey, C. J. Helal, Angew. Chem. 1998, 110, 2092
32. Angew. Chem. Int. Ed. 1998, 37, 1986.
33. J. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512
34. T. R. Hoye, C. S. Jeffrey, F. Shao, Nat. Protoc. 2007, 2, 2451.
35. J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989.
36. M. Scholl, T. M. Trnka, J. P. Morgan, R. H. Grubbs, Tetrahedron Lett. 1999, 40, 2247
37. C. N. Kuzniewski, J. Gertsch, M. Wartmann, K.-H. Altmann, Org. Lett. 2008, 10, 1183.
38. K. Biswas, H. Lin, J. T. Njardarson, M. D. Chappell, T.-C. Chou, Y. Guan, W. P. Tong, L. He, S. B. Horwitz, S. J. Danishefsky, J. Am. Chem. Soc. 2002, 124, 9825.
39. For a review on macrolactonizations see:, A. Parenty, X. Moreau, J.-M. Campagne, Chem. Rev. 2006, 106, 911.
40. L. V. Heumann, G. E. Keck, Org. Lett. 2007, 9, 1951.
41. D. A. Evans, A. H. Hoveyda, J. Am. Chem. Soc. 1990, 112, 6447.
42. S. D. Rychnovsky, Y. Hu, B. Ellsworth, Tetrahedron Lett. 1998, 39, 7271
43. D. J. Kopecky, S. D. Rychnovsky, J. Org. Chem. 2000, 65, 191.
44. R. Jasti, J. Vitale, S. D. Rychnovsky, J. Am. Chem. Soc. 2004, 126, 9904.
45. J. S. Yadav, B. V. SubbaReddy, G. G. K. S. NarayanaKumar, G. MadhusudhanReddy, Chem. Lett. 2007, 36, 426.
46. S. Marumoto, J. J. Jaber, J. P. Vitale, S. D. Rychnovsky, Org. Lett. 2002, 4, 3919.
47. K.-P. Chan, Y. HuiLing, J. Li-TingChan, T.-P. Loh, J. Org. Chem. 2007, 72, 2127
48. H.-W. Hagedorn, R. Brossmer, Helv. Chim. Acta 1986, 69, 2127.
49. S. Hatakeyama, H. Irie, T. Shintani, Y. Noguchi, H. Yamada, M. Nishizawa, Tetrahedron 1994, 50, 13369.
50. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127.
51. D. A. Evans, A. M. Ratz, B. E. Huff, G. S. Sheppard, Tetrahedron Lett. 1994, 35, 7171.
52. J. D. White, R. G. Carter, K. F. Sundermann, M. Wartmann, J. Am. Chem. Soc. 2001, 123, 5407.
53. A. Chan, P. M. Andreae, P. T. Northcote, J. H. Miller, Invest. New Drugs 2011, 29, 615.