Rapid Access to Complex Molecular Architectures via o-Azaquinones

Angewandte Chemie - International Edition

Volumn 40, Issue 11, 2001, Pages 2145-2149

  Nicolaou, K C ^a,b   Zhong, Yong Li ^a,b   Baran, Phil S ^a,b   Sugita, Kazyuki ^a,b  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001463905     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20010601)40:11<2145::AID-ANIE2145>3.0.CO;2-M     Document Type: Article

References (21)

1. a) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625;
2. a) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 636-639; Angew. Chem. Int. Ed. 2000, 39, 622-625;
3. b) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628;
4. b) K. C. Nicolaou, Y.-L. Zhong, P. S. Baran, Angew. Chem. 2000, 112, 639-642; Angew. Chem. Int. Ed. 2000, 39, 625-628;
5. c) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629; Angew. Chem. Int. Ed. 2000, 39, 2525-2529;
6. c) K. C. Nicolaou, P. S. Baran, Y.-L. Zhong, J. A. Vega, Angew. Chem. 2000, 112, 2625-2629; Angew. Chem. Int. Ed. 2000, 39, 2525-2529;
7. d) K. C. Nicolaou, Y.-L. Zhong, P.S. Baran, J. Am. Chem. Soc. 2000, 122, 7596-7597;
8. e) K. C. Nicolaou, P. S. Baran, R. Kranich, Y.-L. Zhong, K. Sugita, N. Zou, Angew. Chem. 2001, 113, 208-212; Angew. Chem. Int. Ed. 2001, 40, 202-206;
9. e) K. C. Nicolaou, P. S. Baran, R. Kranich, Y.-L. Zhong, K. Sugita, N. Zou, Angew. Chem. 2001, 113, 208-212; Angew. Chem. Int. Ed. 2001, 40, 202-206;
10. f) K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, Angew. Chem. 2001, 113, 213-216; Angew. Chem. Int. Ed. 2001, 40, 207-210;
11. f) K. C. Nicolaou, K. Sugita, P. S. Baran, Y.-L. Zhong, Angew. Chem. 2001, 113, 213-216; Angew. Chem. Int. Ed. 2001, 40, 207-210;
12. g) K. C. Nicolaou, P. S. Baran, Z.-L. Zhong, J. Am. Chem. Soc. 2001, 123, 3183-3185.
13. The pseudopterosins are potent anti-inflammatory agents: S. A. Look, W. Fenical, G. Matsumoto, J. Clardy, J. Org. Chem. 1986, 51, 5140-5145; W. Fenical, J. Nat. Prod. 1987, 50, 1001-1008; S. A. Look, W. Fenical, Tetrahedron 1987, 43, 3363-3370. For synthetic studies, see E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777- 12782, and references therein.
14. The pseudopterosins are potent anti-inflammatory agents: S. A. Look, W. Fenical, G. Matsumoto, J. Clardy, J. Org. Chem. 1986, 51, 5140- 5145; W. Fenical, J. Nat. Prod. 1987, 50, 1001-1008; S. A. Look, W. Fenical, Tetrahedron 1987, 43, 3363-3370. For synthetic studies, see E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777- 12782, and references therein.
15. The pseudopterosins are potent anti-inflammatory agents: S. A. Look, W. Fenical, G. Matsumoto, J. Clardy, J. Org. Chem. 1986, 51, 5140- 5145; W. Fenical, J. Nat. Prod. 1987, 50, 1001-1008; S. A. Look, W. Fenical, Tetrahedron 1987, 43, 3363-3370. For synthetic studies, see E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777- 12782, and references therein.
16. The pseudopterosins are potent anti-inflammatory agents: S. A. Look, W. Fenical, G. Matsumoto, J. Clardy, J. Org. Chem. 1986, 51, 5140- 5145; W. Fenical, J. Nat. Prod. 1987, 50, 1001-1008; S. A. Look, W. Fenical, Tetrahedron 1987, 43, 3363-3370. For synthetic studies, see E. J. Corey, S. E. Lazerwith, J. Am. Chem. Soc. 1998, 120, 12777-12782, and references therein.
17. A. D. Rodriguez, E. Gonzalez, S. D. Huang, J. Org. Chem. 1998, 63, 7083-7091.
18. To the best of our knowledge, there have been no reported synthetic studies of a,β-unsaturated ketohydroxyamides such as 1, except for a brief study of the related 3-bromo-2-hydroxy-2-acetamidocyclohexanone, see: K.M. Ermolaev, V. I. Maimind, Biol. Aktiv. Soedin. 1968, 142-146.
19. G. W. Bemis, M. A. Murcko, J. Med. Chem. 1996, 39, 2887.
20. K. C. Nicolaou, P. S. Baran, Y.-L. Zhong. J. Am. Chem. Soc. 2000, 122, 10246-10248.
21. Crystallographic data (excluding structure factors) for the structures 1, 2a, and 3a reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-159145-159147. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road. Cambridge CB2 IEZ. UK (fax: (+ 44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).