Synthesis of the diazepanone-nucleoside core structure of liposidomycins and caprazamycins based on 7-exo cyclization of epoxyamine

Heterocycles

Volumn 88, Issue 1, 2014, Pages 719-730

  Miyaoka, Hiroaki ^a   Wada, Jumpei ^a   Kawashima, Etsuko ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84987622525     PISSN: 03855414     EISSN: 18810942     Source Type: Journal    
DOI: 10.3987/COM-13-S(S)34     Document Type: Article

References (55)

1. (a) K. Isono, M. Uramoto, H. Kusakabe, K. Kimura, K. Izaki, C. C. Nelson, and J. A. McCloskey, J. Antibiot., 1985, 38, 1617
2. (b) M. Ubukata, K. Isono, K. Kimura, C. C. Nelson, and J. A. McCloskey, J. Am. Chem. Soc., 1988, 110, 4416
3. (c) K. Kimura, N. Miyata, G. Kawanishi, Y. Kamio, K. Izaki, and K. Isono, Agric. Biol. Chem., 1989, 53, 1811
4. (d) M. Ubukata, K. Kimura, K. Isono, C. C. Nelson, J. M. Gregson, and J. A. McCloskey, J. Org. Chem., 1992, 57, 6392
5. (e) M. Muroi, K. Kimura, H. Osada, M. Inukai, and A. Takatsuki, J. Antibiot., 1997, 50, 103
6. (f) K. Kimura, S. Kagami, Y. Ikeda, H. Takahashi, M. Yoshihama, H. Kusakabe, H. Osada, and K. Isono, J. Antibiot., 1998, 51, 640
7. (g) K. Kimura, Y. Ikeda, S. Kagami, M. Yoshihama, M. Ubukata, Y. Esumi, H. Osada, and K. Isono, J. Antibiot., 1998, 51, 647
8. (h) K. Kimura, Y. Ikeda, S. Kagami, M. Yoshihama, K. Suzuki, H. Osada, and K. Isono, J. Antibiot., 1998, 51, 1099
9. (i) S. Kagami, K. Kimura, Y. Ikeda, H. Takahashi, H. Kusakabe, H. Osada, K. Isono, and M. Yoshihama, Actinomycetol, 1998, 12, 110.
10. (a) M. Igarashi, N. Nakagawa, N. Doi, S. Hattori, H. Naganawa, and M. Hamada, J. Antibiot., 2003, 56, 580
11. (b) M. Igarashi, Y. Takahashi, T. Shitara, H. Nakamura, H. Naganawa, T. Miyake, and Y. Akamatsu, J. Antibiot., 2005, 58, 327
12. (c) S. Siebenberg, L. Kaysser, E. Wemakor, L. Heide, B. Gust, and B. Kammerer, Rapid Commun. Mass Spectrom., 2011, 25, 495.
13. (a) M. R. Spade, M. Ubukata, and K. Isono, Heterocycles, 1992, 34, 1147
14. (b) S. Knapp, S. Nandan, and L. Resnick, Tetrahedron Lett., 1992, 33, 5485
15. (c) K. S. Kim, I. H. Cho, Y. H. Ahn, and J. I. Park, J. Chem. Soc., Perkin Trans. 1, 1995, 1783
16. (d) W. J. Moore and F. A. Luzzio, Tetrahedron Lett., 1995, 37, 6599
17. (e) K. S. Kim, C. S. Cheong, J. S. Hahn, and J. I. Park, Bull. Korean Chem. Soc., 1997, 18, 465
18. (f) Y. L. Merrer, C. Gravier-Pelletier, M. Gerrouache, and J.-C. Depezay, Tetrahedron Lett., 1998, 39, 385
19. (g) K. S. Kim and Y. H. Ahn, Tetrahedron: Asymmetry, 1998, 9, 3601
20. (h) S. Knapp, G. J. Morriello, S. R. Nandan, T. J. Emge, G. A. Doss, R. T. Mosley, and L. Chen, J. Org. Chem., 2001, 66, 5822
21. (i) C. Gravier-Pelletier, M. Milla, Y. L. Merrer, and J.-C. Depezay, Eur. J. Org. Chem., 2001, 3039
22. (j) S. Knapp, G. J. Morriello, and G. A. Doss, Org. Lett., 2002, 4, 603
23. (k) S. Knapp, G. J. Morriello, and G. A. Doss, Tetrahedron Lett., 2002, 43, 5797
24. (l) N. Nakajima, T. Isobe, S. Irisa, and M. Ubukata, Heterocycles, 2003, 59, 107
25. (m) B. Drouillat, O. Poupardin, Y. Bourdreux, and C. Greck, Tetrahedron Lett., 2003, 44, 2781
26. (n) F. Sarabia, L. Martín-Ortiz, and F. J. López-Herrera, Org. Lett., 2003, 5, 3927
27. (o) C. Gravier-Pelletier, M. Ginisty, and Y. L. Merrer, Tetrahedron: Asymmetry, 2004, 15, 189
28. (p) S. Fukunishi, M. Ubukata, and N. Nakajima, Heterocycles, 2005, 66, 129
29. (q) M. Ginisty, C. Gravier-Pelletier, and Y. L. Merrer, Tetrahedron: Asymmetry, 2006, 17, 142
30. (r) B. Drouillat, Y. Bourdreux, D. Perdon, and C. Greck, Tetrahedron: Asymmetry, 2007, 18, 1955
31. (s) S. Fukunishi, M. Ubukata, and N. Nakajima, Heterocycles, 2007, 73, 627
32. (t) O. Monasson, M. Ginisty, J. Mravljak, G. Bertho, C. Gravier-Pelletier, and Y. L. Merrer, Tetrahedron: Asymmetry, 2009, 20, 2320
33. (u) J. Mravljak, O. Monasson, B. Al-Dabbagh, M. Crouvoisier, A. Bouhss, C. Gravier-Pelletier, and Y. L. Merrer, Eur. J. Med. Chem., 2011, 46, 1582
34. (v) F. Sarabia, C. Vivar-García, C. García-Ruiz, L. Martín-Ortiz, and A. Romero-Carrasco, J. Org. Chem., 2012, 77, 1328.
35. (a) S. Hirano, S. Ichikawa, and A. Matsuda, Angew. Chem. Int. Ed., 2005, 44, 1854
36. (b) S. Hirano, S. Ichikawa, and A. Matsuda, J. Org. Chem., 2007, 72, 9936
37. (c) S. Hirano, S. Ichikawa, and A. Matsuda, J. Org. Chem., 2008, 73, 569
38. (d) S. Hirano, S. Ichikawa, and A. Matsuda, Bioorg. Med. Chem., 2008, 16, 428
39. (e) S. Hirano, S. Ichikawa, and A. Matsuda, Bioorg. Med. Chem., 2008, 16, 5123
40. (f) K. Ii, S. Ichikawa, B. Al-Dabbagh, A. Bouhss, and A. Matsuda, J. Med. Chem., 2010, 53, 3793
41. (g) A. P. Spork, S. Koppermann, B. Dittrich, R. Herbst-Irmer, and C. Ducho, Tetrahedron: Asymmetry, 2010, 21, 763
42. (h) C. Tsukano, S. Yokouchi, A.-L. Girard, T. Kuribayashi, S. Sakamoto, T. Enomoto, and Y. Takemoto, Org. Biomol. Chem., 2012, 10, 6074
43. (i) P. Gopinath, T. Watanabe, and M. Shibasaki, J. Org. Chem., 2012, 77, 9260.
44. (a) M. Sabat and C. R. Johnson, Org. Lett., 2000, 2, 1089
45. (b) R. C. Yanagita, Y. Nakagawa, N. Yamanaka, K. Kashiwagi, N. Saito, and K. Irie, J. Med. Chem., 2008, 51, 46.
46. R. Curci, A. Dinoi, and M. F. Rubio, Pure Appl. Chem., 1995, 67, 811.
47. J. L. Koviach, M. D. Chappell, and R. L. Halcomb, J. Org. Chem., 2001, 66, 2318.
48. X. Cong, F. Hu, K.-G. Liu, Q. J. Liao, and Z. J. Yao, J. Org. Chem., 2005, 70, 4514.
49. Primary amine 7 was chosen as amine segment D, because the chemical yield of the condensation reaction of amine and nucleoside segment was considered.
50. (a) J. M. Tronchet and M. J. Valero, Helv. Chim. Acta, 1979, 62, 2788
51. (b) J. A. Montgomery and H. J. Thomas, J. Org. Chem., 1981, 46, 594
52. (c) K. S. Kim, C. M. Kang, S. J. Kim, K. S. Jung, and C. S. Hahn, Bull. Korean Chem. Soc., 1985, 6, 350
53. (d) K. S. Kim, S. J. Kim, J. H. Kim, and C. S. Hahn, Bull. Korean Chem. Soc., 1989, 10, 116.
54. P. L. Anelli, C. Biffi, F. Montanari, and S. Quici, J. Org. Chem., 1987, 52, 2559.
55. L. A. Carpino, J. Am. Chem. Soc., 1993, 115, 4397.