Two approaches to the aromatic core of the aminonaphthoquinone antibiotics

Journal of Organic Chemistry

Volumn 78, Issue 11, 2013, Pages 5587-5603

  Nawrat, Christopher C ^a   Palmer, Leoni I ^a   Blake, Alexander J ^a   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMOPHORES; CYCLIZATION; KETONES; QUINONE; REACTION INTERMEDIATES;

ANSAMYCINS; AROMATIC CORES; BUILDING BLOCKES; DIELS-ALDER REACTION; MANGANESE ACETATE; NAPHTHOQUINONE; NATURAL PRODUCTS; NATURALLY OCCURRING;

MANGANESE COMPOUNDS;

1 NAPHTHOL; ANSAMYCIN DERIVATIVE; ANTIBIOTIC AGENT; NAPHTHOQUINONE; NATURAL PRODUCT;

ARTICLE; CHROMATOPHORE; CYCLIZATION; DEPROTECTION REACTION; DIELS ALDER REACTION; SYNTHESIS;

EID: 84879307969     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400737f     Document Type: Article

References (46)

1. Thomson, R. H. Naturally Occurring Quinones IV. Recent Advances, 4 th ed.; Blackie: London, 1997.
2. O'Brien, R. J.; Lyle, M. A.; Snider, D. E. Rev. Infect. Dis. 1987, 9, 519-530
3. Brogden, R. N.; Fitton, A. Drugs 1994, 47, 983-1009
4. Matsuda, S.; Adachi, K.; Matsuo, Y.; Nukina, M.; Shizuri, Y. J. Antibiot. 2009, 62, 519-526
5. Cai, P.; Kong, F.; Ruppen, M. E.; Glasier, G.; Carter, G. T. J. Nat. Prod. 2005, 68, 1736-1742
6. Hanessian, S.; Wang, W.; Gai, Y.; Olivier, E. J. Am. Chem. Soc. 1997, 119, 10034-10041
7. Paterson, I.; McClure, C. K.; Schumann, R. C. Tetrahedron Lett. 1989, 30, 1293-1296
8. Roush, W. R.; Coffey, D. S.; Madar, D. J. J. Am. Chem. Soc. 1997, 119, 11331-11332
9. Canova, S.; Bellosta, V.; Bigot, A.; Mailliet, P.; Mignani, S.; Cossy, J. Org. Lett. 2006, 9, 145-148
10. Andrus, M. B.; Meredith, E. L.; Simmons, B. L.; Soma Sekhar, B. B. V.; Hicken, E. J. Org. Lett. 2002, 4, 3549-3552
11. Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873-3888
12. Qin, H.-L.; Panek, J. S. Org. Lett. 2008, 10, 2477-2479
13. Turks, M.; Huang, X.; Vogel, P. Chem.-Eur. J. 2005, 11, 465-476
14. Danishefsky, S. J.; Myles, D. C.; Harvey, D. F. J. Am. Chem. Soc. 1987, 109, 862-867
15. Schetter, B.; Mahrwald, R. Angew. Chem., Int. Ed. 2006, 45, 7506-7525
16. Li, J.; Menche, D. Synthesis 2009, 2293-2315
17. Kishi, Y. Pure Appl. Chem. 1981, 53, 1163-1180
18. Iio, H.; Nagaoka, H.; Kishi, Y. J. Am. Chem. Soc. 1980, 102, 7965-7967
19. Rasapalli, S.; Jarugumilli, G.; Yarrapothu, G. R.; Golen, J. A.; Rheingold, A. L. Tetrahedron Lett. 2013, 54, 2615-2618
20. Citterio, A.; Pesce, L.; Sebastiano, R.; Santi, R. Synthesis 1990, 142-144
21. Jamie, J. F.; Rickards, R. W. J. Chem. Soc., Perkin Trans. 1 1996, 2603-2613
22. Nawrat, C. C.; Lewis, W.; Moody, C. J. J. Org. Chem. 2011, 76, 7872-7881
23. Becker, A. M.; Herlt, A. J.; Hilton, G. L.; Kibby, J. J.; Rickards, R. W. J. Antibiot. 1983, 36, 1323-1328
24. Kibby, J. J.; McDonald, I. A.; Rickards, R. W. J. Chem. Soc., Chem. Commun. 1980, 768-769
25. Anderson, M. G.; Monypenny, D.; Rickards, R. W.; Rothschild, J. M. J. Chem. Soc., Chem. Commun. 1989, 311-313
26. Sensi, P. Pure Appl. Chem. 1975, 41, 15-31
27. Rickards, R. W. Stud. Nat. Prod. Chem. 1991, 9, 431-445
28. Baytekin, B.; Baytekin, H. T.; Hahn, U.; Reckien, W.; Kirchner, B.; Schalley, C. A. Chem.-Eur. J. 2009, 15, 7139-7149
29. Crombie, L.; Jamieson, S. V. J. Chem. Soc., Perkin Trans. 1 1982, 1467-1475
30. Nawrat, C. C.; Moody, C. J. Org. Lett. 2012, 14, 1484-1487
31. Pollet, P.; Gelin, S. Synthesis 1978, 142-143
32. Kimata, A.; Nakagawa, H.; Ohyama, R.; Fukuuchi, T.; Ohta, S.; Suzuki, T.; Miyata, N. J. Med. Chem. 2007, 50, 5053-5056
33. Kuttruff, C. A.; Geiger, S.; Cakmak, M.; Mayer, P.; Trauner, D. Org. Lett. 2012, 14, 1070-1073
34. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y.-L. Angew. Chem., Int. Ed. 2001, 40, 207-210
35. Elban, M. A.; Hecht, S. M. J. Org. Chem. 2008, 73, 785-793
36. Hanessian, S.; Giroux, S.; Larsson, A. Org. Lett. 2006, 8, 5481-5484
37. Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161
38. Becker, A. M.; Rickards, R. W. Aust. J. Chem. 1984, 37, 2103-2109
39. Shi, F.; Smith, M. R.; Maleczka, R. E. Org. Lett. 2006, 8, 1411-1414
40. Chakraborty, T. K.; Reddy, G. V. J. Org. Chem. 1992, 57, 5462-5469
41. Lin, C.-F.; Yang, J.-S.; Chang, C.-Y.; Kuo, S.-C.; Lee, M.-R.; Huang, L.-J. Bioorg. Med. Chem. 2005, 13, 1537-1544
42. Choudhury, A. M. J. Chem. Soc., Perkin Trans. 1 1974, 132-134
43. Michaelides, M. R.; Schoenleber, R.; Thomas, S.; Yamamoto, D. M.; Britton, D. R.; MacKenzie, R.; Kebabian, J. W. J. Med. Chem. 1991, 34, 2946-2953
44. Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549
45. Sugasawa, S.; Yamada, S.-i.; Narahashi, M. Yakugaku Zasshi 1951, 71, 1345-1349
46. Clive, D. L. J.; Bergstra, R. J. J. Org. Chem. 1991, 56, 4976-4977