Synthesis of amino-1,4-benzoquinones and their use in Diels - Alder approaches to the aminonaphthoquinone antibiotics

Journal of Organic Chemistry

Volumn 76, Issue 19, 2011, Pages 7872-7881

  Nawrat, Christopher C ^a   Lewis, William ^a   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDER REACTIONS; BUILDING BLOCKES; DIENOPHILES; NEW PROTOCOL; PROTECTING GROUP;

METHANOL;

ANTIBIOTICS;

1,4 BENZOQUINONE DERIVATIVE; 2 ACETAMIDO 1,4 BENZOQUINONE; 2,5 DIMETHOXYANILINE; 5 HALO 2 AMINOBENZOQUINONE; AMINO 1,4 BENZOQUINONE; AMINONAPHTHOQUINONE ANTIBIOTIC; ANILINE DERIVATIVE; ANTIBIOTIC AGENT; BENZOQUINONE DERIVATIVE; METHANOL; NITROGEN; UNCLASSIFIED DRUG; WATER;

ARTICLE; DIELS ALDER REACTION; OXIDATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BENZOQUINONES; CHEMISTRY TECHNIQUES, SYNTHETIC; ISOMERISM; NAPHTHOQUINONES; OXIDATION-REDUCTION;

EID: 80054111842     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo201320g     Document Type: Article

References (31)

1. Thomson, R. H. Naturally Occurring Quinones IV. Recent Advances, 4th ed.; Blackie: London, 1997.
2. O'Brien, R. J.; Lyle, M. A.; Snider, D. E. Rev. Infecti. 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. Davis, C. J.; Hurst, T. E.; Jacob, A. M.; Moody, C. J. J. Org. Chem. 2005, 70, 4414-4422.
6. McErlean, C. S. P.; Moody, C. J. J. Org. Chem. 2007, 72, 10298-10301.
7. Coombes, C. L.; Moody, C. J. J. Org. Chem. 2008, 73, 6758-6762.
8. Guillonneau, L.; Taddei, D.; Moody, C. J. Org. Lett. 2008, 10, 4505-4508.
9. Padwal, J.; Lewis, W.; Moody, C. J. Org. Biomol. Chem. 2011, 9, 3484-3493.
10. Kulanthaivel, P.; Perun, T. J.; Belvo, M. D.; Strobel, R. J.; Paul, D. C.; Williams, D. C. J. Antibiot. 1999, 52, 256-262.
11. Kelly, T. R.; Behforouz, M.; Echavarren, A.; Vaya, J. Tetrahedron Lett. 1983, 24, 2331-2334.
12. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y. L. Angew. Chem., Int. Ed. 2001, 40, 207-210.
13. Whiteley, C. G. Bioorg. Med. Chem. 2002, 10, 1221-1227.
14. Wipf, P.; Kim, Y. T.; Jahn, H. Synthesis 1995, 1549-1561.
15. Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X. D.; Lewis, N. Synthesis 1998, 775-790.
16. Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Sugita, K. J. Am. Chem. Soc. 2002, 124, 2212-2220.
17. Nicolaou, K. C.; Sugita, K.; Baran, P. S.; Zhong, Y. L. J. Am. Chem. Soc. 2002, 124, 2221-2232.
18. Nicolaou, K. C.; Baran, P. S.; Zhong, Y. L.; Barluenga, S.; Hunt, K. W.; Kranich, R.; Vega, J. A. J. Am. Chem. Soc. 2002, 124, 2233-2244.
19. Tohma, H.; Morioka, H.; Harayama, Y.; Hashizume, M.; Kita, Y. Tetrahedron Lett. 2001, 42, 6899-6902.
20. Nicolaou, K. C.; Baran, P. S.; Kranich, R.; Zhong, Y. L.; Sugita, K.; Zou, N. Angew. Chem., Int. Ed. 2001, 40, 202-206.
21. Courchesne, M.; Brassard, P. J. Nat. Prod. 1993, 56, 722-730.
22. Boisvert, L.; Brassard, P. J. Org. Chem. 1988, 53, 4052-4059.
23. Vela, J.; Zhu, L. W.; Flaschenriem, C. J.; Brennessel, W. W.; Lachicotte, R. J.; Holland, P. L. Organometallics 2007, 26, 3416-3423.
24. Grunwell, J. R.; Karipides, A.; Wigal, C. T.; Heinzman, S. W.; Parlow, J.; Surso, J. A.; Clayton, L.; Fleitz, F. J.; Daffner, M.; Stevens, J. E. J. Org. Chem. 1991, 56, 91-95.
25. Gould, S. J.; Shen, B.; Whittle, Y. G. J. Am. Chem. Soc. 1989, 111, 7932-7938.
26. Lyon, M. A.; Lawrence, S.; Williams, D. J.; Jackson, Y. A. J. Chem. Soc., Perkin Trans. 1 1999, 437-442.
27. Bloom, A. U.S. Patent 2649482, 1953.
28. Gulland, J. M.; Robinson, R.; Scott, J.; Thornley, S. J. Chem. Soc. 1929, 2924-2941.
29. Buttrus, N. H.; Cornforth, J.; Hitchcock, P. B.; Kumar, A.; Stuart, A. S. J. Chem. Soc., Perkin Trans. 1 1987, 851-857.
30. Kelly, T. R.; Echavarren, A.; Behforouz, M. J. Org. Chem. 1983, 48, 3849-3851.
31. Collins, D. J.; Choo, G. L. P.; Obrist, H. Aust. J. Chem. 1990, 43, 617-622