Total synthesis of pacidamycin D by Cu(I)-Catalyzed oxy enamide formation

Organic Letters

Volumn 13, Issue 19, 2011, Pages 5240-5243

  Okamoto, Kazuya ^a   Sakagami, Masahiro ^a   Feng, Fei ^a,b   Togame, Hiroko ^a   Takemoto, Hiroshi ^a   Ichikawa, Satoshi ^b   Matsuda, Akira ^b  

^a SHIONOGI AND CO LTD   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; PACIDAMYCIN 1; PEPTIDE; PYRIMIDINE NUCLEOSIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY;

CATALYSIS; COPPER; MOLECULAR STRUCTURE; PEPTIDES; PYRIMIDINE NUCLEOSIDES;

EID: 80054716538     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol202124b     Document Type: Article

References (37)

1. Winn, M.; Goss, R. J. M.; Kimura, K.-I.; Bugg, T. D. H. Nat. Prod. Rep. 2010, 27, 279-304.
2. Kimura, K.-I.; Bugg, T. D. H. Nat. Prod. Rep. 2003, 20, 252-273.
3. Karwowski, J. P.; Jackson, M.; Theriault, R. J.; Chen, R. H.; Barlow,G. J.;Maus,M. L. J.Antibiot. 1989, 42, 506-511.
4. Chen,R.H.; Buko, A.M.;Whittern,D.N.;McAlpine, J. B. J. Antibiot. 1989, 42, 512-520.
5. Fernandes, P. B.; Swanson, R. N.; Hardy, D. J.; Hanson, C. W.; Coen, L.; Rasmussen, R. R.; Chen, R. H. J. Antibiot. 1989, 42, 521-526.
6. Fronko, R.M.; Lee, J. C.; Galazzo, J. G.; Chamberland, S.;Malouin, F.; Lee,M. D. J. Antibiot. 2000, 53, 1405-1410.
7. Isono, F.; Inukai, M. Antimicrob. Agents Chemother. 1991, 35, 234-236.
8. Inukai, M.; Isono, F.; Takatsuki, A. Antimicrob. Agents Chemother. 1993, 37, 980-983.
9. Bugg, T. D. H.; Lloyd, A. J.; Roper, D. I. Infect. Dis. Drug Targets 2006, 6, 85-106.
10. Kimura, K.; Bugg, T. D. H. Nat. Prod. Rep. 2003, 20, 252-273.
11. Bouhss, A.; Mengin-Lecreulx, D.; Le Beller, D.; Van Heijenoort, J. Mol. Microbiol. 1999, 34, 576-585.
12. Bouhss, A.; Trunkfield, A. E.; Bugg, T. D.; Mengin-Lecreulx, D. FEMS Microbiol. Rev. 2008, 32, 208-33.
13. Al-Dabbagh, B.; Henry, X.; El Ghachi, M.; Auger, G.; Blanot, D.; Parquet, C.; Mengin-Lecreulx, D.; Bouhss, A. Biochemistry 2008, 47, 8919-8928.
14. Boojamra, C. G.; Lemoine, R. C.; Lee, J. C.; Léger, R.; Stein, K. A.; Vernier, N. G.; Magon, A.; Lomovskaya, O.; Martin, P. K.; Chamberland, S.; Lee, M. D.; Hecker, S. J.; Lee, V. J. J. Am. Chem. Soc. 2001, 123, 870-874.
15. Lemoine, R. C.; Magon, A.; Hecker, S. Bioorg. Med. Chem. Lett. 2002, 12, 1121-1123.
16. Boojamra C. G.; Lemoine, R. C.; Blais, J.; Vernier, N. G.; Stein, K. A.; Magon, A.; Chamberland, S.; Hecker, S. J.; Lee, V. J. Bioorg. Med. Chem. Lett. 2003, 13, 3305-3309.
17. Gruschow, S.; Rackham, E. J.; Elkins, B.; Newill, P.; Hill, L. M.; Goss, R. J. M. Chem Bio Chem 2009, 10, 355-360.
18. Gentle, C. A.; Harrison, S. A.; Inukai, M.; Bugg, T. D. H. J. Chem. Soc., Perkin Trans. 1 1999, 1287-1294.
19. Howard, N. I.; Bugg, T. D. H. Bioorg. Med. Chem. 2003, 11, 3083-3099.
20. Bozzoli, A.; Kazmierski, W.; Kennedy, G.; Pasquarello, A.; Pecunioso, A. Bioorg. Med. Chem. Lett. 2000, 10, 2759-2763.
21. Roy, A. D.; Grüschow, S.; Cairns, N.; Goss, R. J. M. J. Am. Chem. Soc. 2010, 132, 12243-12245.
22. Zhang, W.; Ntai, I.; Bolla, M. L.; Malcolmson, S. J.; Kahne, D.; Kelleher, N. L.; Walsh, C. T. J. Am. Chem. Soc. 2011, 133, 5240-5243.
23. Review: Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054-3131.
24. Boojamra, C. G.; Lemoine, R. C.; Lee, J. C.; Lger, R.; Stein, K. A.; Vernier, N. G.; Magon, A.; Lomovskaya, O.; Martin, P. K.; Chamberland, S.; Lee, M. D.; Hecker, S. J.; Lee, V. J. J. Am. Chem. Soc. 2001, 123, 870-874.
25. Majer, P.; Randad, R. S. J. Org. Chem. 1994, 59, 1937-1938.
26. Ogilvie, K. K.; Beaucage, S. L.; Shifman, A. L.; Threiault, N. Y.; Sadana, K. L. Can. J. Chem. 1978, 56, 2768-2780.
27. Jenkins, I. D.; Verheyden, J. P. H.; Moffatt., J. G. J. Am. Chem. Soc. 1971, 93, 4323-4324.
28. Verheyden, J. P. H.; Moffatt., J. G. J. Org. Chem. 1974, 39, 3573-3579.
29. Kumamoto, H.; Onuma, S.; Tanaka, H. J. Org. Chem. 2004, 69, 72-78.
30. Smith, T. H.; Wu, H. Y. J. Org. Chem. 1987, 52, 3566-3573.
31. Gómez, A. M.; Pedregosa, A.; Valverde, S.; López, J. C. Tetrahedron Lett. 2003, 44, 6111-6116.
32. Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809-1812.
33. Jiang, L.; Job, G. E.; Klapars, A.; Buchwald, S. L. Org. Lett. 2003, 5, 3667-3669.
34. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421-7428.
35. The model compound 19 was prepared in 89% yield in a similar manner to the synthesis of 17 from 4 and the corresponding dipeptide carboxamide.
36. Kita, Y.; Sano, A.; Yamaguchi, T.; Oka, M.; Gotanda, K.; Matsugi, M. Tetrahedron Lett. 1997, 38, 3549-3552.
37. Kita, Y.; Gotanda, K.; Murata, K.; Suemura, M.; Sano, A.; Yamaguchi, T.; Oka, M.; Matsugi, M. Org. Process Res. Dev. 1998, 2, 250-254.