Tackling the challenges in the total synthesis of landomycin A

Chemical Record

Volumn 13, Issue 1, 2013, Pages 70-84

  Yang, Xiaoyu ^a   Wang, Ping ^a   Yu, Biao ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

antibiotics; glycosylation; landomycin; natural products; total synthesis

Indexed keywords

AMINOGLYCOSIDE; ANTIINFECTIVE AGENT; LANDOMYCIN A;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; GLYCOSYLATION; STEREOISOMERISM; SYNTHESIS;

AMINOGLYCOSIDES; ANTI-BACTERIAL AGENTS; GLYCOSYLATION; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 84874286074     PISSN: 15278999     EISSN: 15280691     Source Type: Journal    
DOI: 10.1002/tcr.201200018     Document Type: Article

References (73)

1. T. Henkel, J. Rohr, J. M. Beale, L. Schwene, J. Antibiot. 1990, 43, 492.
2. B. P. Matselyukh, T. A. Konovalova, L. V. Polishchuk, O. I. Bambura, Mikrobiol. Z. 1998, 60, 31.
3. a) J. Rohr, R. Thiericke, Nat. Prod. Rep. 1992, 9, 103
4. b) K. Krohn, J. Rohr, Top. Curr. Chem. 1997, 188, 127
5. c) M. K. Kharel, P. Pahari, M. D. Shepherd, N. Tibrewal, S. E. Nybo, K. A. Shaaban, J. Rohr, Nat. Prod. Rep. 2012, 29, 264
6. d) M. K. Kharel, J. Rohr, Curr. Opin. Chem. Biol. 2012, 16, 150.
7. For selected reports on the biosynthesis of landomycins, see: a), S. Weber, C. Zolke, J. Rohr, J. M. Beale, J. Org. Chem. 1994, 59, 4211
8. b) L. Westrich, S. Domann, B. Faust, D. Bedford, D. A. Hopwood, A. Bechthold, FEMS Microbiol. Lett. 1999, 170, 381
9. c) L. Zhu, B. Ostash, U. Rix, M. Nur-e-Alam, A. Mayers, A. Luzhetskyy, C. Mendez, J. A. Salas, A. Bechthold, V. Fedorenko, J. Rohr, J. Org. Chem. 2005, 70, 631
10. d) A. Luzhetskyy, T. Taguchi, M. Fedoryshyn, C. Durr, S. E. Wohlert, V. Novikov, A. Bechthold, ChemBioChem 2005, 6, 1406
11. e) A. Luzhetskyy, M. Fedoryshyn, C. Durr, T. Taguchi, V. Novikov, A. Bechthold, Chem. Biol. 2005, 12, 725
12. f) A. Erb, C. Krauth, A. Luzhetskyy, A. Bechthold, Appl. Microbiol. Biotech. 2009, 83, 1067
13. g) M. K. Kharel, P. Pahari, K. A. Shaaban, G. J. Wang, C. Morris, J. Rohr, Org. Biomol. Chem. 2012, 10, 4256.
14. a) H. Depenbrock, S. Bornschlegl, R. Peter, J. Rohr, P. Schmid, P. Schweighart, T. Block, J. Rastetter, A. R. Kanauske, Ann. Hematol. 1996, 73, A80/316
15. b) R. T. Crow, B. Rosenbaum, R. Smith III, Y. Guo, K. S. Ramos, G. A. Sulikowski, Bioorg. Med. Chem. Lett. 1999, 9, 1663
16. c) A. V. Korynevska, B. P. Matselyukh, R. S. Stoika, Experimental Oncology 2003, 25, 98
17. d) L. Zhu, A. Luzhetskyy, C. Mattingly, V. Adams, A. Bechthold, J. Rohr, ChemBioChem 2007, 8, 83
18. e) A. Korynevska, P. Heffeter, B. Matselyukh, L. Elbling, M. Micksche, R. Stoika, W. Berger, Biochem. Pharmacol. 2007, 74, 1713
19. f) K. A. Shaaban, C. Stamatkin, C. Damodaran, J. Rhor, J. Antibiot. 2011, 64, 141
20. g) K. A. Shaaban, S. Srinivasan, R. Kumar, C. Damodaran, J. Rhor, J. Nat. Prod. 2011, 74, 2.
21. a) Y. Guo, J. J. Lu, G. A. Sulikowski, Abstracts of Papers of the American Chemical Society 1997, 213, 476
22. b) Y. Guo, G. A. Sulikowski, J. Am. Chem. Soc. 1998, 120, 1392.
23. X. Yang, B. Fu, B. Yu, J. Am. Chem. Soc. 2011, 133, 12433.
24. a) K. Kim, Y. Guo, G. A. Sulikowski, J. Org. Chem. 1995, 60, 6866
25. b) D. S. Larsen, M. D. O'Shea, J. Org. Chem. 1996, 61, 5681
26. c) F. M. Hauser, W. A. Dorsch, D. Mal, Org. Lett. 2002, 4, 2237
27. d) K. Ohmori, K. Mori, Y. Ishikawa, H. Tsuruta, S. Kuwahara, N. Harada, K. Suzuki, Angew. Chem. Int. Ed. 2004, 43, 3167
28. e) K. Mori, Y. Tanaka, K. Ohmori, K. Suzuki, Chem. Lett. 2008, 37, 470
29. f) K. Mori, K. Ohmori, K. Suzuki, Angew. Chem. Int. Ed. 2009, 48, 5633
30. g) X. Bugaut, X. Guinchard, E. Roulland, J. Org. Chem. 2010, 75, 8190
31. h) S. Yamaguchi, H. Tanaka, R. Yamada, S. Kawauchi, T. Takahashi, Synlett 2012, 23, 1327
32. i) X. Bugaut, E. Roulland, Eur. J. Org. Chem. 2012, 34, 908.
33. a) C. H. Marzabadi, R. W. Franck, Tetrahedron 2000, 56, 8385
34. b) D. Hou, T. L. Lowary, Carbohydr. Res. 2009, 344, 1911
35. c) A. Borovika, P. Nagorny, J. Carbohydr. Chem. 2012, 31, 255.
36. W. R. Roush, R. J. Neitz, J. Org. Chem. 2004, 69, 4906.
37. P. Wang, PhD Thesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 2005.
38. F. M. Hauser, W. A. Dorsch, D. Mal, Org. Lett. 2002, 4, 2237.
39. a) N. Flahatpisheh, G. A. Sulikowski, Synlett 1994, 672
40. b) K. Sobti, K. Kim, G. A. Sulikowski, J. Org. Chem. 1996, 61, 6.
41. a) S. Hashimoto, A. Sano, H. Sakamoto, M. Nakajima, Y. Yanagiya, S. Ikegabi, Synlett 1995, 1271
42. b) I. Peterson, M. McLeod, Tetrahedron Lett. 1995, 36, 9065.
43. A. Kirschning, Eur. J. Org. Chem. 1998, 2267.
44. a) W. R. Roush, K. Briner, D. P. Sebesta, Synlett 1993, 264
45. b) W. R. Roush, C. E. Bennett, J. Am. Chem. Soc. 1999, 121, 3541
46. c) W. R. Roush, B. W. Gung, C. E. Bennett, Org. Lett. 1999, 1, 891.
47. W. R. Roush, C. E. Bennett, J. Am. Chem. Soc. 2000, 122, 6124.
48. H. Tanaka, A. Yoshizawa, T. Takahashi, Angew. Chem. Int. Ed. 2007, 46, 2505.
49. H. Tanaka, S. Yamaguchi, A. Yoshizawa, M. Takagi, K. Shin-ya, T. Takahashi, Chem. Asian J. 2010, 5, 1407.
50. F. E. McDonald, K. S. Reddy, Y. Díaz, J. Am. Chem. Soc. 2000, 122, 4304.
51. F. E. McDonald, K. S. Reddy, J. Organomet. Chem. 2001, 617-618, 444.
52. a) R. S. Babu, M. Zhou, G. A. O'Doherty, J. Am. Chem. Soc. 2004, 126, 3428
53. b) M. Zhou, G. A. O'Doherty, Org. Lett. 2006, 8, 4339.
54. M. Zhou, G. A. O'Doherty, Org. Lett. 2008, 10, 2283.
55. H. Yu, PhD Thesis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 2000.
56. F.-I. Auzanneau, D. R. Bundle, Carbohydr. Res. 1991, 212, 13.
57. a) B. Yu, Z. Yang, Tetrahedron Lett. 2000, 41, 2961
58. b) Z. Yang, B. Yu, Carbohydr. Res. 2001, 333, 105.
59. Z. Yang, H. Cao, J. Hu, R. Shan, B. Yu, Tetrahedron 2003, 59, 249.
60. B. Yu, Z. Yang, Org. Lett. 2001, 3, 377.
61. P. Wang, B. Yu, Org. Let. 2002, 4, 1919.
62. X. Yang, PhD Thesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 2012.
63. a) G. Grynkiewica, Carbohydr. Res. 1977, 53, C11
64. b) K. Akerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. 1979, B33
65. c) P. J. Garegg, T. Iversen, T. Norberg,. Carbohydr. Res. 1979, 73, 313
66. d) W. R. Roush, X. F. Lin, J. Org. Chem. 1991, 56, 5740
67. e) W. R. Roush, X. F. Lin, J. Am. Chem. Soc. 1995, 117, 2236
68. f) G. Gao, O. Schwardt, B. Ernst, Carbohydr. Res. 2004, 339, 2835.
69. S. N. Lam, J. Gervay-Hague, Org. Lett. 2003, 5, 4219.
70. a) B. Yu, H. Tao, Tetrahedron Lett. 2001, 42, 2405
71. b) B. Yu, J. Sun, Chem. Commun. 2010, 46, 4668
72. c) B. Yu, J. Sun, X. Yang, Acc. Chem. Res. 2012, 45, 1227.
73. W. R. Roush, C. E. Bennentt, S. E. Roberts, J. Org. Chem. 2001, 66, 6389.