Stereoselective total synthesis of tubulysin v

Chinese Journal of Chemistry

Volumn 31, Issue 1, 2013, Pages 40-48

  Wang, Rui ^a   Tian, Ping ^a   Lin, Guoqiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

aza Barbier reaction; indium; N tert butanesulfinyl imines; tubulysin V; zinc

Indexed keywords

EID: 84872701836     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201200984     Document Type: Article

References (42)

1. Sasse, F.,;, Steinmetz, H.,;, Heil, J.,;, Höfle, G.,;, Reichenbach, H.,. J. Antibiot., 2000, 53, 879.
2. Steinmetz, H.,;, Glaser, N.,;, Herdtweck, E.,;, Sasse, F.,;, Reichenbach, H.,;, H?fle, G.,. Angew. Chem., Int. Ed., 2004, 43, 4888.
3. Steinmetz, H.,;, Glaser, N.,;, Herdtweck, E.,;, Sasse, F.,;, Reichenbach, H.,;, Höfle, G.,. Angew. Chem., 2004, 116, 4996.
4. Dömling, A.,;, Richter, W.,. Mol. Divers., 2005, 9, 141.
5. Khalil, M.,;, Sasse, F.,;, Lv̈nsdorf, H.,;, Elnakady, Y.,;, Reichenbach, H.,. ChemBioChem, 2006, 7, 678.
6. Kaur, G.,;, Hollingshead, M.,;, Holbeck, S.,;, Schauer- Vukašinovic̈, V.,;, Camalier, R. F.,;, Dömling, A.,;, Agarwal, S.,. Biochem. J., 2006, 396, 235.
7. Peltier, H. M.,;, McMahon, J. P.,;, Patterson, A. W.,;, Ellman, J. A.,. J. Am. Chem. Soc., 2006, 128, 16018.
8. Dömling, A.,;, Beck, B.,;, Eichelberger, U.,;, Sakamuri, S.,;, Menon, S.,;, Chen, Q.-Z.,;, Lu, Y.-C.,;, Wessjohann, L. A.,. Angew. Chem., Int. Ed., 2006, 45, 7235. Angew. Chem., Int. Ed., 2007, 46, 2347 (corrigenda)
9. Sani, M.,;, Fossati, G.,;, Huguenot, F.,;, Zanda, M.,. Angew. Chem., Int. Ed., 2007, 46, 3526.
10. Patterson, A. W.,;, Peltier, H. M.,;, Sasse, F.,;, Ellman, J. A.,. Chem. Eur. J., 2007, 13, 9534.
11. Raghavan, B.,;, Balasubramanian, R.,;, Steele, J. C.,;, Sackett, D. L.,;, Fecik, R. A.,. J. Med. Chem., 2008, 51, 1530.
12. Balasubramanian, R.,;, Raghavan, B.,;, Begaye, A.,;, Sackett, D. L.,;, Fecik, R. A.,. J. Med. Chem., 2009, 52, 238.
13. Patterson, A. W.,;, Peltier, H. M.,;, Ellman, J. A.,. J. Org. Chem., 2008, 73, 4362.
14. Chandrasekhar, S.,;, Mahipal, B.,;, Kavitha, M.,. J. Org. Chem., 2009, 74, 9531.
15. Friestad, G. K.,;, Marié, J.-C.,;, Deveau, A. M.,. Org. Lett., 2004, 6, 3249.
16. Wipf, P.,;, Takada, T.,;, Rishel, M. J.,. Org. Lett., 2004, 6, 4057.
17. Shankar, P. S.,;, Sani, M.,;, Terraneo, G.,;, Zanda, M.,. Synlett, 2009, 1341.
18. Shibue, T.,;, Hirai, T.,;, Okamoto, I.,;, Morita, N.,;, Masu, H.,;, Azumaya, I.,;, Tamura, O.,. Tetrahedron Lett., 2009, 50, 3845.
19. Ullrich, A.,;, Herrmann, J.,;, Müller, R.,;, Kazmaier, U.,. Eur. J. Org. Chem., 2009, 6367.
20. Pando, O.,;, Dörner, S.,;, Preusentanz, R.,;, Denkert, A.,;, Porzel, A.,;, Richter, W.,;, Wessjohann, L.,. Org. Lett., 2009, 11, 5567.
21. Shibue, T.,;, Hirai, T.,;, Okamoto, I.,;, Morita, N.,;, Masu, H.,;, Azumaya, I.,;, Tamura, O.,. Chem. Eur. J., 2010, 16, 11678.
22. Shibue, T.,;, Hirai, T.,;, Okamoto, I.,;, Morita, N.,;, Masu, H.,;, Isao Azumaya, I.,;, Tamura, O.,. Chem. Eur. J., 2010, 16, 11678.
23. Shibue, T.,;, Okamoto, I.,;, Morita, N.,;, Morita, H.,;, Hirasawa, Y.,;, Hosoya, T.,;, Tamura, O.,. Bioorg. Med. Chem. Lett., 2011, 21, 431.
24. Vlahov, I. R.,;, Wang, Y.,;, Vetzel, M.,;, Hahn, S.,;, Kleindl, P. J.,;, Reddy, J. A.,;, Leamon, C. P.,. Bioorg. Med. Chem. Lett., 2011, 21, 6778.
25. Burkhart, J. L.,;, Müller, R.,;, Kazmaier, U.,. Eur. J. Org. Chem., 2011, 3050.
26. Shankar, P. S.,;, Sani, M.,;, Saunders, F. R.,;, Wallace, H. M.,;, Zanda, M.,. Synlett, 2011, 1673.
27. Pando, O.,;, Stark, S.,;, Denkert, A.,;, Porzel, A.,;, Preusentanz, R.,;, Wessjohann, L. A.,. J. Am. Chem. Soc., 2011, 133, 7692.
28. Burkhart, J. L.,;, Kazmaier, U.,. RSC Adv., 2012, 2, 3785.
29. Becker, D.,;, Kazmaier, U.,. J. Org. Chem., 2012, asap, DOI: dx.doi.org/10.1021/jo301693d.
30. Sun, X.-W.,;, Xu, M.-H.,;, Lin, G.-Q.,. Org. Let., 2006, 8, 4979.
31. Sun, X.-W.,;, Liu, M.,;, Xu, M.-H.,;, Lin, G.-Q.,. Org. Lett., 2008, 10, 1259.
32. Liu, M.,;, Sun, X.-W.,;, Xu, M.-H.,;, Lin, G.-Q.,. Chem. Eur. J., 2009, 15, 10217.
33. Liu, M.,;, Shen, A.,;, Sun, X.-W.,;, Deng, F.,;, Xu, M.-H.,;, Lin, G.-Q.,. Chem. Commun., 2010, 8460.
34. Shen, A.,;, Liu, M.,;, Jia, Z-S.,;, Xu, M.-H.,;, Lin, G.-Q.,. Org. Lett., 2010, 12, 5154.
35. Touré, B. B.,;, Hall, D. G.,. Chem. Rev., 2009, 109, 4439.
36. Reddy, L. R.,;, Hu, B.,;, Prashad, M.,;, Prasad, K.,. Org. Lett., 2008, 10, 3109.
37. Bower, J. F.,;, SÌvenda, J.,;, Williams, A. J.,;, Charmant, J. P. H.,;, Lawrence, R. M.,;, Szeto, P.,;, Gallagher, T.,. Org. Lett., 2004, 6, 4727.
38. Claver, C.,;, Fernandez, E.,;, Gillon, A.,;, Heslop, K.,;, Hyett, D. J.,;, Martorell, A.,;, Orpen, A. G.,;, Pringle, P. G.,. Chem. Commun., 2000, 961.
39. Toujas, J.-L.,;, Jost, E.,;, Vaultier, M.,. Bull. Soc. Chim. Fr., 1997, 134, 713.
40. Greene's Protective Groups in Organic Synthesis, 4 th ed., Eds.:, Wuts, P. G. M.,;, Greene, T. W., John Wiley & Sons, Hoboken, 2007.
41. Movassaghi, M.,;, Hunt, D. K.,;, Tjandra, M.,. J. Am. Chem. Soc., 2006, 128, 8126.
42. Hirano, S.,;, Ichikawa, S.,;, Matsuda, A.,. Tetrahedron, 2007, 63, 2798.