Synthesis and Biological Evaluation of Lactimidomycin and Its Analogues

Chemistry - A European Journal

Volumn 21, Issue 52, 2015, Pages 19159-19167

  Larsen, Brian J ^a   Sun, Zhankui ^a   Lachacz, Eric ^a   Khomutnyk, Yaroslav ^a   Soellner, Matthew B ^a   Nagorny, Pavel ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

anticancer activity; biological evaluation; lactimidomycin; macrocyclization; total synthesis

Indexed keywords

CELLS; CHAINS; CONDENSATION REACTIONS; KETONES;

ANTICANCER ACTIVITIES; BIOLOGICAL EVALUATION; LACTIMIDOMYCIN; MACRO-CYCLIZATION; TOTAL SYNTHESIS;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; BIOLOGICAL FACTOR; GLUTARIMIDE; LACTIMIDOMYCIN; LACTONE; MACROLIDE; PIPERIDONE DERIVATIVE; ZINC;

CELL MOTION; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DRUG EFFECTS; HUMAN; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BIOLOGICAL FACTORS; CELL MOVEMENT; CYCLIZATION; HUMANS; LACTONES; MACROLIDES; MOLECULAR STRUCTURE; PIPERIDONES; STEREOISOMERISM; ZINC;

EID: 84954532704     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201503527     Document Type: Article

References (78)

1. K. Sugawara, Y. Nishiyama, S. Toda, N. Komiyama, M. Hatori, T. Moriyama, Y. Sawada, H. Kamei, M. Konishi, O. Toshikazu, J. Antibiotics 1992, 45, 1433;
2. K. Nakae, Y. Yoshimoto, T. Sawa, T. Y. Homma, Y. M. Hamada, T. Takeuchi, M. Imoto, J. Antibiotics 2000, 53, 1130;
3. E. J. Woo, C. M. Starks, C. Jr. Carney, R. Arslanian, L. Cadapan, S. Zavala, P. Licari, J. Antibiotics 2002, 55, 141;
4. S. R. Rajski, B. Shen, ChemBioChem 2010, 11, 1951;
5. D. Yang, X. Zhu, X. Wu, Z. Feng, L. Huang, B. Shen, Y. Zhang, Appl. Microbiol. Biotechnol. 2011, 89, 1709;
6. S.-X. Huang, Z. Yu, F. Robert, L.-X. Zhao, Y. Jiang, Y. Duan, J. Pelletier, B. Shen, J. Antibiot. 2011, 64, 164;
7. S. Lee, B. Liu, S. Lee, S.-X. Huang, B. Shen, S.-B. Qian, Proc. Natl. Acad. Sci. USA 2012, 109, 14728;
8. M. Ma, T. Kwong, S.-K. Lim, J. R. Lohman, B. Shen, J. Am. Chem. Soc. 2013, 135, 2489;
9. M. Yin, Y. Yan, J. R. Lohman, S.-X. Huang, M. Ma, G.-R. Zhao, L.-H. Xu, W. Xiang, B. Shen, Org. Lett. 2014, 16, 3072;
10. N. G. De Loubresse, I. Prokhorova, W. Holtkamp, M. V. Rodnina, G. Yusupova, M. Yusupov, Nature 2014, 513, 517;
11. T. Schneider-Poetsch, J. Ju, D. E. Eyler, Y. Dang, S. Bhat, W. C. Merrick, R. Green, B. Shen, J. O. Jun, Nature Chem. Biol. 2010, 6, 209;
12. M. A. Walczak, S. J. Danishefsky, in Synthesis of Antimetastatic Agents Using Ring-Closing Metathesis, Handbook of Metathesis, 2 nd ed., (Ed.: R. H. Grubbs,), Wiley-VCH, Weinheim 2015, pp. 574.
13. C. Gaul, J. T. Njardarson, S. J. Danishefsky, J. Am. Chem. Soc. 2003, 125, 6042;
14. J. T. Njardarson, C. Gaul, D. Shan, X.-Y. Huang, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 1038;
15. C. Gaul, J. T. Njardarson, D. Shan, D. C. Dorn, K.-D. Wu, W. P. Tong, X.-Y. Huang, M. A. S. Moore, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 11326;
16. P. Nagorny, I. Krauss, J. T. Njardarson, L. Perez, C. Gaul, G. Yang, O. Ouerfelli, S. J. Danishefsky, Tetrahedron Lett. 2010, 51, 3873.
17. D. Shan, L. Chen, J. T. Njardarson, C. Gaul, X. Ma, S. J. Danishefsky, X.-Y. Huang, Proc. Natl. Acad. Sci. USA 2005, 102, 3772;
18. T. Oskarsson, P. Nagorny, I. J. Krauss, L. Perez, M. Mandal, G. Yang, O. Ouerfelli, D. Xiao, M. A. S. Moore, J. Massague, S. J. Danishefsky, J. Am. Chem. Soc. 2010, 132, 3224;
19. N. Lecomte, J. T. Njardarson, P. Nagorny, G. Yang, R. Downey, O. Ouerfelli, M. A. S. Moore, S. J. Danishefsky, Proc. Natl. Acad. Sci. USA 2011, 108, 15074.
20. J. Ju, S. R. Rajski, S.-K. Lim, J.-W. Seo, N. R. Peters, F. M. Hoffman, B. Shen, J. Am. Chem. Soc. 2009, 131, 1370.
21. K. Micoine, P. Persich, J. Llaveria, M.-H. Lam, A. Maderna, F. Loganzo, A. Furstner, Chem. Eur. J. 2013, 19, 7370.
22. J. Ju, S.-K. Lim, H. Jiang, B. Shen, J. Am. Chem. Soc. 2005, 127, 1622;
23. J. Ju, S.-K. Lim, H. Jiang, J.-W. Seo, B. Shen, J. Am. Chem. Soc. 2005, 127, 11930;
24. J. Ju, S.-K. Lim, H. Jiang, J.-W. Seo, Y. Her, B. Shen, Org. Lett. 2006, 8, 5865;
25. J. Ju, J.-W. Seo, Y. Her, S.-K. Lim, B. Shen, Org. Lett. 2007, 9, 5183.
26. T. Schneider-Poetsch, Ph.D. Thesis 2009, John Hopkins University, p. 33.
27. I. J. Krauss, M. Mandal, S. J. Danishefsky, Angew. Chem. Int. Ed. 2007, 46, 5576;
28. Angew. Chem. 2007, 119, 5672.
29. K. Micoine, A. Furstner, J. Am. Chem. Soc. 2010, 132, 14064;
30. D. Gallenkamp, A. Furstner, J. Am. Chem. Soc. 2011, 133, 9232.
31. Total synthesis of lactimidomycin:, B. J. Larsen, Z. Sun, P. Nagorny, Org. Lett. 2013, 15, 2998.
32. T. Nagasawa, S. Kuwahara, Org. Lett. 2013, 15, 3002.
33. During the preparation of this manuscript, a formal total synthesis of lactimidomycin based on copper-catalyzed ene-yne coupling/alkyne reductive macrocyclization was reported:, W. Li, G. I. Georg, Chem. Commun. 2015, 51, 8634.
34. N. R. Cichowicz, P. Nagorny, Org. Lett. 2012, 14, 1058;
35. Z. Sun, G. A. Winschel, A. Borovika, P. Nagorny, J. Am. Chem. Soc. 2012, 134, 8074;
36. P. Nagorny, Z. Sun, G. A. Winschel, Synlett 2013, 661;
37. A. Borovika, P. Nagorny, Tetrahedron 2013, 69, 5719;
38. E. Mensah, N. Camasso, W. Kaplan, P. Nagorny, Angew. Chem. Int. Ed. 2013, 52, 12932;
39. Angew. Chem. 2013, 125, 13170;
40. A. Borovika, P.-I. Tang, S. Klapman, P. Nagorny, Angew. Chem. Int. Ed. 2013, 52, 13424;
41. Angew. Chem. 2013, 125, 13666;
42. B. Bhattarai, J.-H. Tay, P. Nagorny, Chem. Commun. 2015, 51, 5398;
43. Z. Sun, G. A. Winschel, P. Zimmerman, P. Nagorny, Angew. Chem. Int. Ed. 2014, 53, 11194;
44. Angew. Chem. 2014, 126, 11376;
45. J.-H. Tay, A. J. Arguelles, P. Nagorny, Org. Lett. 2015, 17, 3774.
46. A. B. Smith III, J. W. Leahy, I. Noda, S. W. Remiszewski, N. J. Liverton, R. Zibuck, J. Am. Chem. Soc. 1992, 114, 2995.
47. T. Neubauer, C. Kammerer-Pentier, T. Bach, Chem. Commun. 2012, 48, 11629.
48. K. Ando, K. Narumiya, H. Takada, T. Teruya, Org. Lett. 2010, 12, 1460;
49. H. E. Giesbrecht, B. J. Knight, N. R. Tanguileg, C. R. Emerson, P. R. Blakemore, Synlett 2010, 374.
50. C. Napolitano, P. McArdle, P. V. Murphy, J. Org. Chem. 2010, 75, 7404.
51. M. A. Blanchette, W. Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush, T. Sakai, Tetrahedron Lett. 1984, 25, 2183.
52. M. W. Rathke, M. Nowak, J. Org. Chem. 1985, 50, 2624;
53. S. Sano, K. Yokoyama, M. Fukushima, T. Yagi, Y. Nagao, Chem. Commun. 1997, 559;
54. M. Katayama, R. Nagase, K. Mitarai, T. Misaki, Y. Tanabe, Synlett 2006, 129;
55. T. D. W. Claridge, S. G. Davies, J. A. Lee, R. L. Nicholson, P. M. Roberts, A. J. Russell, A. D. Smith, S. M. Toms, Org. Lett. 2008, 10, 5437.
56. Intermolecular version:
57. D. J. Schauer, P. Helquist, Synthesis 2006, 3654; Application to the formation of macrolactams:
58. M. C. Pirrung, M. G. Biswas, T. R. Ibarra-Rivera, Org. Lett. 2010, 12, 2402.
59. S.-I. Shirokawa, M. Kamiyama, T. Nakamura, M. Okada, A. Nakazaki, S. Hosokawa, S. Kobayashi, J. Am. Chem. Soc. 2004, 126, 13604;
60. A. Schmauder, S. Muller, M. E. Maier, Tetrahedron 2008, 64, 6263.
61. D. A. Evans, J. Bartroli, T. L. Shih, J. Am. Chem. Soc. 1981, 103, 2127.
62. D. A. Evans, P. Nagorny, K. J. McRae, D. J. Reynolds, L.-S. Sonntag, F. Vounatsos, R. Xu, Angew. Chem. Int. Ed. 2007, 46, 537;
63. Angew. Chem. 2007, 119, 543;
64. D. A. Evans, P. Nagorny, D. T. Reynolds, K. J. McRae, Angew. Chem. Int. Ed. 2007, 46, 541;
65. Angew. Chem. 2007, 119, 547;
66. D. A. Evans, P. Nagorny, K. J. McRae, L.-S. Sonntag, D. J. Reynolds, F. Vounatsos, Angew. Chem. Int. Ed. 2007, 46, 545;
67. Angew. Chem. 2007, 119, 551.
68. R. J. Corriu, J. Masse, D. Samate, J. Organomet. Chem. 1975, 93, 71;
69. D. M. Hodgson, C. Wells, Tetrahedron Lett. 1992, 33, 4761.
70. I. C. Stewart, C. J. Douglas, R. H. Grubbs, Org. Lett. 2008, 10, 441.
71. G. Stork, K. Zhao, Tetrahedron Lett. 1989, 30, 2173.
72. Beaver-Goodman, K. Ph.D. Thesis 2003, Harvard University.
73. S. A. Frank, H. Chen, R. K. Kunz, M. J. Schnaderbeck, W. R. Roush, Org. Lett. 2000, 2, 2691.
74. J.-I. Uenishi, J.-M. Beau, R. W. Armstrong, Y. Kishi, J. Am. Chem. Soc. 1987, 109, 4756.
75. R. Martin, S. L. Buchwald, Acc. Chem. Res. 2008, 41, 1461;
76. E. A. B. Kantchev, C. J. O'Brien, M. G. Organ, Angew. Chem. Int. Ed. 2007, 46, 2768;
77. Angew. Chem. 2007, 119, 2824.
78. J. S. Potuzak, D. S. Tan, Tetrahedron Lett. 2004, 45, 1797.