New and concise syntheses of the bicyclic oxamazin core using an intramolecular nitroso diels-alder reaction and ring-closing olefin metathesis

Organic Letters

Volumn 15, Issue 2, 2013, Pages 358-361

  Watson, Kyle D ^a   Carosso, Serena ^a   Miller, Marvin J ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BETA LACTAM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; CYCLOADDITION; STEREOISOMERISM; SYNTHESIS;

ALKENES; BETA-LACTAMS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOADDITION REACTION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84872565596     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303305u     Document Type: Article

References (24)

1. Dürckheimer, W.; Blumbach, J.; Lattrell, R.; Scheunemann, K. H. Angew. Chem., Int. Ed. 1985, 24, 180
2. Christensen, B. G. Chem. Br. 1989, 25, 371
3. Walsh, C. Nature 2000, 406, 775
4. Walsh, C. Antibiotics: Actions, Origins, Resistance; ASM Press: Washington, D.C., 2003.
5. Woulfe, S. R.; Miller, M. J. Tetrahedron Lett. 1984, 25, 3293
6. Cohen, N. C. J. Med. Chem. 1983, 26, 259
7. Kronethal, D.; Kuester, P.; Koster, W. H. Abstracts from the Tenth International Congress of Heterocyclic Chemistry, Abstract G3-25, 1985.
8. Ghosh, M.; Miller, M. J. Tetrahedron 1996, 52, 4225
9. Zercher, C. K.; Miller, M. J. Tetrahedron Lett. 1989, 30, 7009
10. Sparks, S. M.; Chow, C. P.; Zhu, L.; Shea, K. J. J. Org. Chem. 2004, 69, 3025
11. Keck, G. E. Tetrahedron Lett. 1978, 19, 4767
12. Keck, G. E.; Webb, R. R.; Yates, J. B. Tetrahedron 1981, 37, 4007
13. Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem, Int. Ed. 1995, 34, 2039
14. Schwab, R.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 110
15. Barrett, A. G. M.; Baugh, S. P. D.; Braddock, C.; Flack, K.; Gibson, V. C.; Giles, M. R.; Marshall, E. L.; Procopiou, P. A.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1998, 63, 7893
16. Alcaide, B.; Almendros, P.; Alonso, J. M.; Redondo, M. C. J. Org. Chem. 2003, 68, 1426
17. Frietag, D.; Schwab, P.; Metz, P. Tetrahedron Lett. 2004, 45, 3589
18. Lennartz, M.; Steckhan, E. Synlett 2000, 3, 319
19. Yang, Y.-K.; Tae, J. Synlett 2003, 7, 1043
20. Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026
21. Miller, M. J.; Mattingly, P. G. Tetrahedron 1983, 39, 2563
22. Miller, M. J. J. Acc. Chem. Res. 1986, 19, 49
23. Mitsunobu, O. Synthesis 1981, 1
24. Humphrey, G. R.; Miller, R. A.; Pye, P. J.; Rossen, K.; Reamer, R. A.; Miliakal, A.; Ceglia, S. S.; Grabowski, E. J. J.; Volante, R. P; Reider, P. J. J. Am. Chem. Soc. 1999, 121, 11261