Diastereoselective synthesis of cyclopentapyridazinones via radical cyclization: Synthetic studies toward halichlorine

Organic Letters

Volumn 10, Issue 21, 2008, Pages 4783-4786

  Keck, Gary E ^a   Neumann, Stacey A ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOPENTANE DERIVATIVE; FREE RADICAL; HALICHLORINE; HETEROCYCLIC COMPOUND; PYRIDAZINE DERIVATIVE; SPIRO COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; AZA COMPOUNDS; CYCLIZATION; CYCLOPENTANES; FREE RADICALS; MOLECULAR STRUCTURE; PYRIDAZINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 58149161581     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801849u     Document Type: Article

References (53)

1. (a) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
2. (b) Marco-Contelles, J.; Ruiz, P.; Sanchez, B.; Jimeno, M. L. Tetrahedron Lett. 1992, 33, 5261.
3. (c) Curran, D. P.; Sisko, J.; Yeske, P. E.; Liu, H. Pure Appl. Chem. 1993, 65, 1153.
4. (d) Keck, G. E.; Wager, T. T.; McHardy, S. F. J. Org. Chem. 1998, 63, 9164.
5. (a) Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564.
6. (b) Stork, G.; Mook, R.; Biller, S. A.; Rychnovsky, S. D. J. Am. Chem. Soc. 1983, 105, 3741.
7. (c) Choi, J.-K.; Hart, D. J. Tetrahedron 1985, 41, 3959.
8. (d) Fukuzawa, S.-i; Tsuchimoto, T. Synlett 1993, 803.
9. (e) Miyata, O.; Nishiguchi, A.; Nmomiya, I.; Aoe, K.; Okamura, K.; Naito, T. J. Org. Chem. 2000, 65, 6922.
10. For examples of hydrazone acceptors, see: (a) Sturino, C. F.; Fallis, A. G. J. Am. Chem. Soc. 1994, 116, 7447.
11. (b) Marco-Contelles, J.; Balme, G.; Bouyssi, D.; Destabel, C.; Henriet-Bernard, C. D.; Gritnaldi, J.; Hatem, J. M. J. Org. Chem. 1997, 62, 1202.
12. (c) Tauh, P.; Fallis, A. G. J. Org. Chem. 1999, 64, 6960.
13. (d) Friestad, G. K.; Fioroni, G. M. Org. Lett. 2005, 7, 2393.
14. For examples of imine acceptors, see: (e) Tomaszewski, M. J.; Warkentin, J. Chem. Commun. 1993, 966.
15. (f) Bowman, W. R.; Stephenson, P. T.; Terrett, N. K.; Young, A. R. Tetrahedron Lett. 1994, 55, 6369.
16. (g) Kim, S.; Yoon, K. S.; Kim, Y. S. Tetrahedron 1997, 53, 73.
17. For examples of N-aziridinylimine acceptors, see: (h) Kim, S.; Kee, I. S.; Lee, S. J. Am. Chem. Soc. 1991, 113, 9882.
18. (i) Lee, H.-Y.; Kim, D-L; Kim, S. Chem. Commun. 1996, 1539
19. For examples of oxime acceptors, see: (j) Keck, G. E.; Wager, T. T. J. Org. Chem. 1996, 61, 8366.
20. (k) Miyata, O.; Muroya, K.; Koide, J.; Naito, T. Synlett 1998, 271.
21. (l) Keck, G. E.; Wager, T. T.; Rodriquez, J. F. D. J. Am. Chem. Soc. 1999, 121, 5176.
22. (m) Clive, D. L. J.; Pham, M. P.; Subedi, R. J. Am. Chem. Soc. 2007, 129, 2713.
23. (a) Parker, K. A.; Spero, D. M.; Van Epp, J. J. Org. Chem. 1988, 53, 4628.
24. (b) Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Chem. Lett. 1990, 315.
25. (c) Booth, S. E.; Jenkins, P. R.; Swain, C. J.; Sweeney, J, B. J. Chem. Soc., Perkin Trans. 1 1994, 3499.
26. (d) Clive, D. L. J.; Zhang, J.; Subedi, R.; Bouetard, V.; Hiebert, S.; Ewanuk, R. J. Org. Chem, 2001, 66, 1233.
27. (a) Myers, A. G.; Yang, B. G.; Chen. H.; Gleason, J. L. J. Am. Chem. Soc. 1994, 116, 9361.
28. (b) Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. J.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
29. During our initial studies, the enantiomer of the compounds shown in Schemes 2, 3, 5, and 6 was used. For simplicity, only one enantiomer is consistently shown throughout all schemes.
30. (a) El Hashash, M. A.; El Kady, M. Y.; Mohamed, M. M. Ind. J. Chem. Sect. B: Org. Chem. Ind. Med. Chem. 1979, 18, 136.
31. (b) Best, W. M.; Brown, R. F. C.; Tiso, P. D.; Watson, K. G. Aunt. J. Chem. 1990, 43, 427.
32. (c) Essawy, S. A. Ind. J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 1991, 30, 371.
33. (a) Cignarella, G.; Barlocco, D.; Pinna, G. A.; Loriga, M.; Curzu, M. M.; Tofanetti, O.; Germini, M.; Cazzulani, P.; Cavalletti, E. J. Med. Chem. 1989, 32, 2277.
34. (b) Combs, D. W.; Rampulla, M. S.; Demers, J. P.; Falotico, R.; Moore, J, B. J. Med. Chem. 1992, 35, 172.
35. (c) Stajer, G.; Szabo, A.; Bernath, G.; Sonar, P. Heterocycles 1994, 38, 1061.
36. For total syntheses of halichlorine, see: (a) Trauner, D.; Schwarz, J. B.; Danishefslcy, S. J. Angew. Chem., Int. Ed. 1999, 35, 3542.
37. (b) Christie, H. S.; Heathcock, C. H. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 12079.
38. For a comprehensive review of synthetic approaches, see: (c) Clive, D. L. J.; Yu, M.; Wang, J.; Yeh, V. S. C.; Kang, S. Chem. Rev. 2005, 105, 4483.
39. For recent synthetic approaches not covered in ref 9c, see: Andrade, R. B.; Martin, S. F. Org. Lett. 2005, 7, 5733.
40. (e) Kim, H.; Seo, J. H.; Shin, K. J.; Kim, D. J.; Kim, D. Heterocycles 2006, 70, 143.
41. (f) Sinclair, A.; Arini, L. G.; Rejzek, M.; Szeto, P.; Stockman, R. A. Synlett 2006, 14, 2321.
42. (g) Hurley, P. B.; Dake, G. R. J. Org. Chem. 2008, 73, 4231.
43. Kuramoto, M.; Tong, C.; Yamada, K.; Chiba, T.; Hayashi, Y.; Uemura, D. Tetrahedron Lett. 1996, 37, 3867.
44. (a) Bevilacqua, M. P.; Nelson, R. M.; Mannori, G.; Cecconi, O. Annu. Rev. Med. 1994, 45, 361.
45. (b) Carlos, T. M.; Harlan, J. M. Blood 1994, 84, 2068.
46. (c) Foster, C. A. J. Allergy Clin. Immunol. 1996, 98, S270.
47. (d) Yusuf-Makagiansar, H.; Anderson, M. E.; Yakovleva, T. V.; Murray, J. S.; Siahaan, T. J. Med. Res. Rev. 2002, 22, 146.
48. The more obvious sequence of alkylation after radical cyclization was found to give much lower levels of diastereoselectivity for introduction of the methyl group (ca. 2:1).
49. (a) Ding, H.; Friestad, G. K. Org. Lett. 2004, 6, 637.
50. (b) Friestad, G. K.; Marie, J.-C.; Deveau, A. M. Org. Lett. 2004, 6, 3249.
51. (a) Keck, G. E.; Tarbet, K. H.; Geraci, L. S. J. Am. Chem. Soc. 1993, 115, 8467.
52. (b) Keck, G. E.; Krishnamurthy, D. Org. Synth. 1998, 75, 12.
53. See intermediate 6 in ref 9a.