Diaryl ether containing N-hydroxycarbamates from nitroso cycloadducts

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2268-2271

  Bolger, Joshua ^a   Miller, Marvin ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

Bisaryl ether; Hetero Diels Alder; Lipoxygenase; Regioselective ring opening; Transcarbamoylation

Indexed keywords

ALUMINUM OXIDE; BENZYL BROMIDE; CARBAMIC ACID; COPPER; ETHER; LIPOXYGENASE; NITROSO DERIVATIVE; PHENOL;

ALKYLATION; ARTICLE; CARBAMOYLATION; CATALYSIS; DEPROTECTION REACTION; RING OPENING; SYNTHESIS;

ALNUS;

EID: 79953230097     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.016     Document Type: Article

References (24)

1. (a) Ottenheim, H. C. J.; Herscheid, J. D. M. Chem. Rev. 1986, 86, 697;
2. (b) Chimiak, A.; Milewska, M. J. Prog. Chem. Org. Nat. Prod. 1988, 53, 203;
3. (c) Marmion, C. Euro. J. Inorg. Chem. 2004, 15, 3003;
4. (d) Michaelides, M. R.; Curtin, M. L. Cur. Pharm. Des. 1999, 5, 787.
5. Surman, M. D.; Mulvihill, M. J.; Miller, M. J. J. Org. Chem. 2002, 67, 4115.
6. (a) Samuelsson, B. Science 1983, 220, 568-575;
7. (b) Brash, A. R. J. Biol. Chem. 1999, 274, 23679-23682;
8. (c) Steinhilber, D. Pharm. Acta Helv. 1994, 69, 3.
9. (a) Young, R. N. Euro. J. Med. Chem. 1999, 34, 671-685;
10. (b) Rubin, P.; Mollison, K. W. Prostaglandins 2007, 83, 188-197.
11. Bolger, J. K.; Tian, W.; Wolter, W. R.; Cho, W.; Suckow, M. A.; Miller, M. J. Org. Biomol. Chem. 2011. doi:10.1039/C.OB00714E.
12. Surman, M. D.; Mulvihill, M. J.; Miller, M. J. Tetrahedron Lett. 2002, 43, 1131.
13. Backvall, J.-E.; Sellen, M.; Grant, B. J. Am. Chem. Soc. 1990, 112, 6615.
14. 3 290.1756, found 290.1753.
15. Kwon, S.; Myers, A. G. J. Am. Chem. Soc. 2005, 127, 16796-16797.
16. Pelter, A.; Hussain, A.; Smith, G.; Ward, R. S. Tetrahedron 1997, 53, 3879-3916.
17. Lindley, J. Tetrahedron 1984, 40, 1433-1456.
18. (a) Comdom, R. F. P.; Palacios, M. L. D. Syn. Commun. 2003, 33, 921;
19. (b) Palomo, C.; Oiarbide, M.; Lopez, R.; Gomez-Bengoa, E. Chem. Commun. 1998, 2091- 2092;
20. (c) Nicolaou, K. C.; Boddy, C. N. C.; Li, H.; Koumbis, A. E.; Hughes, R.; Natarajan, S.; Jain, N. F.; Ramanjulu, J. M.; Bräse, S.; Solomon, M. E. Chem. Eur. J. 1999, 5, 2602-2621.
21. (a) Evans, D. A.; Katz, J. L.; West, T. R. Tetrahedron Lett. 1998, 39, 2937-2940;
22. (b) Chan, D. M. T.; Monaco, K. L.; Wang, R.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
23. Vauthey, I.; Valot, F.; Gozzi, C.; Fache, F.; Lemaire, M. Tetrahedron Lett. 2000, 41, 6347-6350.
24. 5 369.1654, found 370.1649.