Synthesis of macrocyclic amides using manganese(III)-based intramolecular cyclization of N-(ω-Alkenyl)-3-oxobutanamides

Heterocyclic Communications

Volumn 15, Issue 6, 2009, Pages 467-471

  Ito, Yosuke ^a   Nishino, Hiroshi ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

Intramolecular cyclization; Macrocyclic amides; Macrocyclization; Manganese(III) acetate; Oxidation

Indexed keywords

EID: 77954076862     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.2009.15.6.467     Document Type: Article

References (36)

1. (a) Ouyang, J.; Nishino, H.; Kurosawa, K. J. Heterocycl. Chem. 1995, 32, 1783-1791.
2. (b) Yoshinaga, T.; Nishino, H.; Kurosawa, K. Tetrahedron Lett. 1998, 39, 9197-9200.
3. Chowdhury, F. A.; Nishino, H.; Kurosawa, K. Heterocycl. Commun. 1999, 5, 111-112.
4. Jogo, S.; Nishino, H.; Yasutake, M.; Shinmyozu, T. Tetrahedron Lett. 2002, 43, 9031-9034.
5. (a) Smith, III, A. B.; Wood, J. L.; Wong, W.; Gould, A. E.; Rizzo, C. J.; Barbosa, J.; Komiyama, K.; Omura, S. J. Am. Chem. Soc. 1996, 118, 8308-8315.
6. (b) Xu, Z.; Johannes, C. W.; Houri, A. F.; La, D. S.; Cogan, D. A.; Hofilena, G. E.; Hoveyda, A. H. J. Am. Chem. Soc. 1997, 119, 10302-10316.
7. c) Creighton, C. J.; Reitz, A. B. Org Lett. 2001, 3, 893-895.
8. d) Chow, C. P.; Shea, K. J.; Sparks, S. M. Org Lett. 2002, 4, 2637-2640.
9. (e) Liu, L.; Chen, Q.; Wu, Y.-D.; Li, C. J. Org. Chem. 2005, 70, 1539-1544.
10. (f) Llàcer, E.; Urpí, F.; Vilarrasa, J. Org Lett. 2009, 11, 3198-3201.
11. (a) Mitchell, S. S.; Nicholson, B.; Teisan, S.; Lam, K. S.; Potts, B. C. M. J. Nat. Prod. 2004, 67, 1400-1402.
12. (b) Araki, H.; Matsushima, Y.; Eguchi, T.; Shindo, K.; Kakinuma, K. Tetrahedron Lett. 1998, 39, 3181-3184.
13. c) Otsuka, M.; Eguchi, T.; Shindo, K.; Kakinuma, K. Tetrahedron Lett. 1998, 39, 3185-3188.
14. d) Kudo, F.; Kakinuma, K.; Eguchi, T. Tetrahedron Lett. 2006, 47, 1529-1532.
15. (e) Bode, H. B.; Müller, R. Angew. Chem. Int. Ed. 2007, 46, 2147-2150.
16. (a) Umezawa, I.; Takeshima, H.; Komiyama, K.; Koh, Y.; Yamamoto, H.; Kawaguchi, M. J. Antibiot. 1981, 34, 256-265.
17. (b) Smith, III, A. B.; Rano, T. A.; Chida, N.; Sulikowski, G. A. J. Org. Chem. 1990, 55, 1136-1138.
18. c) Smith, III, A. B.; Rano, T. A.; Chida, N.; Sulikowski, G. A.; Wood, J. A. J Am. Chem. Soc. 1992, 114, 8008-8022.
19. d) Touré, B. B.; Hall, D. G. Chem. Rev. 2009, 109, 4439-4486.
20. (a) Nazaré, M.; Waldmann, H. Angew. Chem. Int. Ed. 2000, 39, 1125-1128.
21. (b) Nazaré, M.; Waldmann, H. Chem. Eur. J. 2001, 7, 3363-3376.
22. (a) Suh, Y.-G.; Kim, S.-A.; Jung, J.-K.; Shin, D.-Y.; Min, K.-H.; Koo, B.-A.; Kim, H.-S. Angew. Chem. Int. Ed 1999, 38, 3545-3547.
23. (b) Liang, B.; Negishi, E. Org Lett. 2008, 10, 193-195.
24. Clive, D. L. J.; Huang, X. Chem. Commun. 2003, 2062-2063.
25. 20/hexane. The analytical samples were further purified by recrystallization from the appropriate solvent.
26. 3N 420.2539 (M+H). Found 420.2534.
27. 3N 378.2069 (M+H). Found 378.2064.
28. w = 0.0497; GOF = 1.448.
29. (a) Tsubusaki, T.; Nishino, H. Heterocycl. Commun. 2009, 1, 79-83.
30. (b) Tsubusaki, T.; Nishino, H. Tetrahedron 2009, 65, 9448-9459.
31. c) Asahi, K.; Nishino, H. Synthesis 2009, 409-423.
32. d) Cong, Z-Q.; Nishino, H. Synthesis 2008, 2686-2694.
33. (e) Asahi, K.; Nishino, H. Heterocycl. Commun. 2008, 14, 21-26.
34. (f) Asahi, K.; Nishino, H. Tetrahedron 2008, 64, 1620-1634.
35. (a) Snider, B. B. Tetrahedron 2009, 65, 10738-10744.
36. (b) Demir, A. S.; Emrullahoglu, M. Cur. Org. Synth. 2007, 4 ,321-351.