Synthesis of peroxylactones using Mn(III)-catalyzed aerobic oxidation

Heterocycles

Volumn 83, Issue 8, 2011, Pages 1783-1805

  Haque, Md Aminul ^a   Nishino, Hiroshi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79961155857     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-11-12241     Document Type: Article

References (60)

1. a) D. A. Casteel, Nat. Prod. Rep., 1992, 9, 289;
2. b) D. J. Faulkner, Nat. Prod. Rep., 1998, 15, 113;
3. c) D. A. Casteel, Nat. Prod. Rep., 1999, 16, 55.
4. a) I. Weissbuch and L. Leiserowitz, Chem. Rev., 2008, 108, 4899;
5. b) O. Provot, B. Camuzat-Dedenis, M. Hamzaoui, H. Moskowitz, J. Mayrargue, A. Robert, J. Cazelles, B. Meunier, F. Zouhiri, D. Desmaële, J. d'Angelo, J. Mahuteau, F. Gay, and L. Cicéron, Eur. J. Org. Chem., 1999, 1935;
6. c) A. Robert, O. Dechy-Cabaret, J. Cazelles, and B. Meunier, Acc. Chem. Res., 2002, 35, 167;
7. R. K. Haynes, W.-Y. Ho, H.-W. Chan, B. Fugmann, J. Stetter, S. L. Croft, L. Vivas, W. Peters, and B. Ld). Robinson, Angew. Chem. Int. Ed., 2004, 43, 1381;
8. e) C. H. Posner and A. M. O'Neill, Acc. Chem. Res., 2004, 37, 397;
9. f) A. M. Szpilman, E. E. Korshin, R. Hoos, G. H. Posner, and M. D. Bachi, J. Org. Chem., 2001, 66, 6531.
10. D. Cremer, 'General and Theoretical Aspects of the Peroxide Group' in 'The Chemistry of Peroxides,' ed. by S. Patai, Wiley, New York, 1983, pp. 1-84.
11. Acidic media: a) H. Nishino, S. Tategami, T. Yamada, J. D. Korp, and K. Kurosawa, Bull. Chem. Soc. Jpn., 1991, 64, 1800;
12. b) M. Sakata, Y. Shirakawa, N. Kamata, Y. Sakaguchi, H. Nishino, J. Ouyang, and K. Kurosawa, J. Heterocycl. Chem., 2000, 37, 269;
13. c) K. Asahi and H. Nishino, Eur. J. Org. Chem., 2008, 2404.
14. Basic media: a) J. Ouyang H, Nishino, and K. Kurosawa, J. Heterocycl. Chem., 1996, 33, 1291;
15. b) C.-Y. Qian, T. Yamada, H. Nishino, and K. Kurosawa, Bull. Chem. Soc. Jpn., 1992, 65, 1371;
16. c) K. Asahi and H. Nishino, Tetrahedron, 2005, 61, 11107;
17. d) F. Najjar, L. Gorrichon, M. Baltas, C. André-Barrès, and H. Vial, Org. Biomol. Chem., 2005, 3, 1612.
18. a) O. Zvarec, T. D. Avery, D. K. Taylor, and E. R. T. Tiekink, Tetrahedron, 2010, 66, 1007;
19. b) T. D. Avery, D. K. Taylor, and E. R. T. Tiekink, J. Org. Chem., 2000, 65, 5531;
20. c) B. W. Greatrex and D. K. Taylor, J. Org. Chem., 2005, 70, 470.
21. G. Banda and I. E. Chakravarthy, Tetrahedron: Asymmetry, 2006, 17, 1684.
22. a) J. L. Oller-López, M. Iranzo, S. Mormeneo, E. Oliver, J. M. Cuerva, and J. E. Oltra, Org. Biomol. Chem., 2005, 3, 1172;
23. b) T. D. Avery, D. Caiazza, J. A. Culbert, D. K. Taylor, and E. R. T. Tiekink, J. Org. Chem., 2005, 70, 8344.
24. a) B. S. Davidson, Tetrahedron Lett., 1991, 32, 7167;
25. b) P. A. Horton, R. E. Longley, M. Kelly-Borges, O. J. McConnell, and L. M. Ballas, J. Nat. Prod., 1994, 57, 1374;
26. c) M. Varoglu, B. M. Peters, and P. Crews, J. Nat. Prod., 1995, 58, 27;
27. d) A. Qureshi, J. Salvá, M. K. Harper, and D. J. Faulkner, J. Nat. Prod., 1998, 61, 1539;
28. e) Y. Chen, K. B. Killday, P. J. McCarthy, R. Schimoler, K. Chilson, C. Selitrennikoff, S. A. Pomponi, and A. E. Wright, J. Nat. Prod., 2001, 64, 262;
29. f) T. L. Perry, A. Dickerson, A. A. Khan, R. K. Kondru, D. N. Beratan, P. Wipf, M. Kelly, and M. T. Hmann, Tetrahedron, 2001, 57, 1483;
30. g) A. Rudi, R. Afanii, L. G. Gravalos, M. Aknin, E. Gaydou, J. Vacelet, and Y. Kashman, J. Nat. Prod., 2003, 66, 682.
31. T. Tsubusaki and H. Nishino, Tetrahedron, 2009, 65, 3745.
32. a) A. Mallinger, T. L. Gall, and C. Mioskowski, J. Org. Chem., 2009, 74, 1124;
33. b) H. Anke, H. Schwab, and H. Achenbach, J. Antibiot., 1980, 33, 931;
34. c) R. Schobert, Naturwissenschaften, 2007, 94, 1;
35. d) D. Tejedor and F. García-Tellado, Org. Prep. Proced. Int., 2004, 36, 33;
36. e) A. L. Zografos and D. Georgiadis, Synthesis, 2006, 3157;
37. f) R. Schobert and A. Schlenk, Bioorg. Med. Chem., 2008, 16, 4203;
38. g) V. Weber, C. Rubat, E. Duroux, C. Lartigue, M. Madesclaire, and P. Coudert, Bioorg. Med. Chem., 2005, 13, 4552.
39. a) C.-Y. Qian, H. Nishino, K. Kurosawa, and J. D. Korp, J. Org. Chem., 1993, 58, 4448;
40. b) M. T. Rahman, H. Nishino, and C.-Y. Qian, Tetrahedron Lett., 2003, 44, 5225;
41. c) M. T. Rahman and H. Nishino, Tetrahedron, 2003, 59, 8383;
42. d) R. Kumabe and H. Nishino, Teteahedron Lett., 2004, 45, 703.
43. F. A. Chowdhury, H. Nishino, and K. Kurosawa, Heterocycles, 1999, 51, 575.
44. a) T. Kametani, T. Katoh, M. Tsubuki, and T. Honda, Chem. Pharm. Bull., 1987, 35, 2334;
45. b) Z. Zorn and R. Lett, Tetrahedron Lett., 2006, 47, 4325;
46. c) T. Kametani, T. Katoh, M. Tsubuki, and T. Honda, J. Am. Chem. Soc., 1986, 108, 7055;
47. d) M. P. Sibi, M. T. Sorum, J. A. Bender, and J. A. Gaboury, Synth. Commun., 1992, 22, 809;
48. e) A. Svendsen and P. M. Boll, Tetrahedron, 1973, 29, 4251;
49. f) T. P. C. Mulholland, R. Foster, and D. B. Haydock, J. Chem. Soc., Perkin Trans. 1, 1972, 1225;
50. g) J. D. White, T. Nishiguchi, and R. W. Skeean, J. Am. Chem. Soc., 1982, 104, 3923.
51. a) G. C. Paddon-Jones, C. M. Moore, D. J. Brecknell, W. A. König, and W. Kitching, Tetrahedron Lett., 1997, 38, 3479;
52. b) H. B. Mereyala and R. R. Gadikota, Chem. Lett., 1999, 273;
53. c) H. B. Mereyala, R. R. Gadikota, K. S. Sunder, and S. Shailaja, Tetrahedron, 2000, 56, 3021;
54. d) J. L. Oller-López, M. Iranzo, S. Mormeneo, E. Oliver, J. M. Cuerva, and J. E. Oltra, Org. Biomol. Chem., 2005, 3, 1172;
55. e) S. Varugese, S. Thomas, S. Haleema, T. Puthiaparambil, and I. Ibnusaud, Tetrahedron Lett., 2007, 48, 82092.
56. K. Asahi and H. Nishino, Tetrahedron, 2008, 64, 1620.
57. a) H. Nishino, 'Bioactive Heterocycles I: Manganese(III)-Based Peroxidation of Alkenes to Heterocycles,' ed. by S. Eguchi, Springer, Berlin, 2006, pp. 39-76 and references cited therein;
58. B. B. Snider, Tetrahedron, 2009, 65, 10738 and references cited thereinb).
59. F. A. Chowdhury, S. Kajikawa, H. Nishino, and K. Kurosawa, Tetrahedron Lett., 1999, 40, 3765.
60. E. I. Heiba, R. M. Dessau, and W. J. Koehl, Jr., J. Am. Chem. Soc., 1969, 91, 138.