Iron(III)/NaBH 4-mediated additions to unactivated alkenes: Synthesis of novel 20′-vinblastine analogues

Organic Letters

Volumn 14, Issue 6, 2012, Pages 1428-1431

  Leggans, Erick K ^a   Barker, Timothy J ^a   Duncan, Katharine K ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BORANE DERIVATIVE; FERRIC ION; SODIUM BOROHYDRIDE; VINBLASTINE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKENES; BOROHYDRIDES; CATALYSIS; FERRIC COMPOUNDS; MOLECULAR STRUCTURE; VINBLASTINE;

EID: 84858665556     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300173v     Document Type: Article

References (41)

1. Noble, R. L. Biochem. Cell Biol. 1990, 68, 1344
2. Noble, R. L.; Beer, C. T.; Cutts, J. H. Ann. N.Y. Acad. Sci. 1958, 76, 882
3. Noble, R. L. Lloydia 1964, 27, 280
4. Svoboda, G. H.; Nuess, N.; Gorman, M. J. Am. Pharm. Assoc. Sci. Ed. 1959, 48, 659
5. The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic: San Diego, 1990; Vol. 37.
6. Potier, P. J. Nat. Prod. 1980, 43, 72
7. Kutney, J. P. Acc. Chem. Res. 1993, 26, 559
8. Ishikawa, H.; Colby, D. A.; Boger, D. L. J. Am. Chem. Soc. 2008, 130, 420
9. Ishikawa, H.; Colby, D. A.; Seto, S.; Va, P.; Tam, A.; Kakei, H.; Rayl, T. J.; Hwang, I.; Boger, D. L. J. Am. Chem. Soc. 2009, 131, 4904
10. Va, P.; Campbell, E. L.; Robertson, W. M.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 8489
11. Sasaki, Y.; Kato, D.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 13533
12. Tam, A.; Gotoh, H.; Robertson, W. M.; Boger, D. L. Bioorg. Med. Chem. Lett. 2010, 20, 6408
13. Gotoh, H.; Duncan, K. K.; Robertson, W. M.; Boger, D. L. ACS Med. Chem. Lett. 2011, 2, 948
14. Ishikawa, H.; Elliott, G. I.; Velcicky, J.; Choi, Y.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 10596
15. Kato, D.; Sasaki, Y.; Boger, D. L. J. Am. Chem. Soc. 2010, 132, 3685
16. Waser, J.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2005, 127, 8294
17. Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J. Am. Chem. Soc. 2006, 128, 11693
18. Baumberger, F.; Vasella, A. Helv. Chim. Acta 1983, 66, 2210
19. Northrup, F. J.; Sears, T. J. J. Chem. Phys. 1990, 93, 2337
20. Gaspar, B.; Carreira, E. M. Angew. Chem., Int. Ed. 2008, 47, 5758
21. Druliner, J. D. Macromolecules 1991, 24, 6079
22. Kianmehr, E.; Baghersad, M. H. Adv. Synth. Catal. 2011, 353, 2599
23. Barton, D. H. R.; Jaszbere, R.; Jaszberenyi, J. C.; Theodorakis, E. A. Tetrahedron 1992, 48, 2613
24. Gaspar, B.; Carreira, E. Angew. Chem., Int. Ed. 2007, 46, 4519
25. Okamoto, T.; Oka, S. J. Org. Chem. 1984, 49, 1589
26. Sugimori, T.; Horike, S.-I.; Tsumura, S.; Handa, M.; Kasuga, K. Inorg. Chem. Acta 1998, 283, 275
27. Taniguchi, T.; Goto, N.; Nishibata, A.; Ishibashi, H. Org. Lett. 2010, 12, 112
28. Taniguchi, T.; Ishibashi, H. Org. Lett. 2010, 12, 124
29. 2, see: Bianchini, C.; Laschi, F.; Peruzzini, M.; Ottaviani, F. M.; Vacca, A.; Zanello, P. Inorg. Chem. 1990, 29, 3394
30. 2O or air, see: Glavee, G. N.; Klabunde, K. J.; Sorensen, C. M.; Hadjipanayis, G. C. Inorg. Chem. 1995, 34, 28
31. Borman, L. S.; Kuehne, M. E. In The Alkaloids; Brossi, A.; Suffness, M., Eds.; Academic: San Diego, 1990; Vol. 37, p 133.
32. Gigant, B.; Wang, C.; Ravelli, R. B. G.; Roussi, F.; Steinmetz, M. O.; Curmi, P. A.; Sobel, A.; Knossow, M. Nature 2005, 435, 519
33. Miller, J. C.; Gutowski, G. E.; Poore, G. A.; Boder, G. B. J. Med. Chem. 1977, 20, 409
34. Miller, J. C.; Gutowski, G. E. Ger. Patent 2753791
35. Chem. Abstr. 1978, 89, 129778.
36. Gerzon, K.; Miller, J. C. Eur. Patent 55602
37. Chem. Abstr. 1982, 97, 163310.
38. Review of superacid functionalization: Duflos, A.; Kruczynski, A.; Baret, J.-M. Curr. Med. Chem. Anti-Cancer Agents 2002, 2, 55
39. Isayama, S.; Mukaiyama, T. Chem. Lett. 1989, 1071
40. 3 alkene nitrosation, see: Kato, K.; Mukaiyama, T. Chem. Lett. 1992, 1137
41. Fringuelli, F.; Pizzo, F.; Vaccaro, L. Synthesis 2000, 646