Discovery of hypoiodite-mediated aminyl radical cyclization lacking a nitrogen radical-stabilizing group: Application to synthesis of an oxazaspiroketal-containing cephalostatin analog

Organic Letters

Volumn 13, Issue 18, 2011, Pages 4766-4769

  Koag, Myong ^a   Lee, Seongmin ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; FREE RADICAL; HYPOIODOUS ACID; IODINE DERIVATIVE; NITROGEN; SPIRO COMPOUND; STEROID;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

AMINES; CYCLIZATION; FREE RADICALS; IODINE COMPOUNDS; MOLECULAR CONFORMATION; NITROGEN; OXIDATION-REDUCTION; SPIRO COMPOUNDS; STEREOISOMERISM; STEROIDS;

EID: 80052701178     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol2017033     Document Type: Article

References (52)

1. Pettit, G. R.; Inoue, M.; Herald, D. L.; Krupa, T. S. J. Am. Chem. Soc. 1988, 110, 2006
2. Pettit, G. R.; Inoue, M.; Kamano, Y.; Herald, D. L. J. Chem. Soc. Chem. Commun. 1988, 1440
3. Pettit, G. R.; Xu, J. P. Bioorg. Med. Chem. Lett. 1995, 5, 2027
4. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1994, 59, 6164
5. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1997, 62, 4484
6. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1997, 62, 4484
7. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. Tetrahedron 1995, 51, 6707
8. Flessner, T.; Jautelat, R.; Scholz, U.; Winterfeldt, E. Prog. Chem. Org. Nat. Prod. 2004, 87, 1
9. Moser, B. R. J. Nat. Prod. 2008, 71, 487
10. Lee, S.; LaCour, T. G.; Fuchs, P. L. Chem. Rev. 2009, 109, 2275
11. Full NCI-60 results for cephalostatins 1-9 (NSC# 363979-81, 378727-36) are on the Web at http://dtp.nci.nih.gov.
12. LaCour, T. G. Ph.D. Thesis, Purdue University, 2001.
13. Jeong, J. U.; Sutton, S. C.; Kim, S.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 10157
14. Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd, M. R. J. Am. Chem. Soc. 1996, 118, 10672
15. LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692
16. Lee, J. S.; Fuchs, P. L. J. Am. Chem. Soc. 2005, 127, 13122
17. Phillips, S. T.; Shair, M. D. J. Am. Chem. Soc. 2007, 129, 6589
18. Cham, B. E.; Daunter, B. Cancer Lett. 1990, 55, 221
19. Cham, B. E.; Meares, H. M. Cancer Lett. 1987, 36, 111
20. Liu, L. F.; Liang, C. H.; Shiu, L. Y.; Lin, W. L.; Lin, C. C.; Kuo, K. W. FEBS Lett. 2004, 577, 67
21. Cherney, E. C.; Baran, P. S. Isr. J. Chem. 2011, 51, 391
22. Rahman, A.; Choudhary, M. I. Nat. Prod. Rep. 1999, 16, 619
23. Kim, Y. C.; Che, Q. -M; Gunatilaka, A. A. L.; Kingston, D. G. I. J. Nat. Prod. 1996, 59, 283
24. Lee, S.; LaCour, T. G.; Lantrip, D.; Fuchs, P. L. Org. Lett. 2002, 4, 313
25. Lee, S.; Fuchs, P. L. Org. Lett. 2002, 4, 317
26. Lee, S.; Fuchs, P. L. Org. Lett. 2004, 6, 1437
27. Lee, S.; Fuchs, P. L. Org. Lett. 2009, 11, 5
28. Uhle, F. C. J. Am. Chem. Soc. 1953, 75, 2280
29. Uhle, F. C. J. Am. Chem. Soc. 1961, 83, 1460
30. Zha, X.; Sun, H.; Zhang, Y. Chem. Biodiversity 2007, 4, 25
31. Wei, G.; Wang, J.; Du, Y. Bioorg. Med. Chem. Lett. 2011, 21, 2930
32. Meystre, C.; Heusler, K.; Kalvoda, J.; Wieland, P.; Anner, G.; Wettstein, A. Helv. Chim. Acta 1962, 45, 1317
33. Danishefsky, S. J.; Armistead, D. M.; Wincott, F. E.; Selnick, H. G.; Hungate, R. J. Am. Chem. Soc. 1987, 109, 8117
34. Hernandez, R.; Velazquez, S. M.; Suárez, E.; Rodriguez, M. S. J. Org. Chem. 1994, 59, 6395
35. Betancor, C.; Freire, R.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2002, 4, 1295
36. Francisco, C. G.; Freire, R.; Herrera, A. J.; Martín, I. P.; Suárez, E. Org. Lett. 2002, 4, 1959-3337
37. Lee, J. S.; Fuchs, P. L. Org. Lett. 2003, 5, 2247
38. Neale, R. S. Synthesis 1971, 1
39. Baldwin, S. W.; Doll, R. J. Tetrahedron Lett. 1979, 20, 3275
40. Betancor, C.; Concepción, J. I.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Org. Chem. 1983, 48, 4430
41. Armas, P.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans I 1988, 3255
42. Carrau, R.; Hernández, R.; Suárez, E.; Betancor, C. J. Chem. Soc., Perkin Trans I 1987, 937
43. Dorta, R. L.; Francisco, C. G.; Suárez, E. J. Chem. Soc., Chem. Comm. 1989, 1168
44. Martín, A.; Pérez-Martín, I.; Suárez, E. Org. Lett. 2005, 7, 2027
45. Armas, P.; Carrau, R.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1985, 26, 2493
46. Togo., H.; Hoshina, Y.; Muraki, T.; Nakayma, H.; Yokoyama, M. J. Org. Chem. 1998, 63, 5193
47. Nikishin, G. I.; Troyansky, F.; Lazareva, M. I. Tetrahedron Lett. 1985, 26, 1877
48. Francisco, C. G.; Herrera, A. J.; Suárez, E. J. Org. Chem. 2003, 68, 1012
49. Hernández, R.; Medina, M. C.; Suárez, E. Tetrahedron Lett. 1987, 28, 2533
50. Guo, C.; Bhandaru, S.; Fuchs, P. L.; Boyd., M. R. J. Am. Chem. Soc. 1996, 118, 10672
51. LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692
52. Li, W.; LaCour, T. G.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 4548