Benzothiazines in synthesis. A total synthesis of pseudopteroxazole

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3581-3583

  Harmata, Michael ^a   Hong, Xuechuan ^a  

^a UNIVERSITY OF MISSOURI   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DITERPENE; OXAZOLE DERIVATIVE; PSEUDOPTEROXAZOLE; THIAZINE DERIVATIVE; TUBERCULOSTATIC AGENT;

ANIMAL; ANTHOZOA; ARTICLE; CHEMISTRY; SYNTHESIS;

ANIMALS; ANTHOZOA; ANTITUBERCULAR AGENTS; DITERPENES; OXAZOLES; THIAZINES;

EID: 23944487696     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0515412     Document Type: Article

References (19)

1. Rodriguez, A. D.; Ramirez, C.; Rodriguez, I. I.; Gonzalez, E. Org. Lett. 1999, 1, 527.
2. Johnson, T. W.; Corey, E. J. J. Am. Chem. Soc. 2001, 123, 4475.
3. Davidson, J. P.; Corey, E. J. J. Am. Chem. Soc. 2003, 125, 13486.
4. Heckrodt, T. J.; Mulzer, J. Top. Curr. Chem. 2005, 244, 1.
5. Harmata, M.; Hong, X. J. Am. Chem. Soc. 2003, 125, 5754.
6. Harmata, M.; Hong, X.; Barnes, C. L. Tetrahedron Lett. 2003, 44, 7261.
7. Harmata, M.; Hong, X. Tetrahedron Lett. 2005, 46, 3847.
8. Harmata, M.; Hong, X.; Barnes, C. L. Org. Lett. 2004, 6, 2201.
9. Stereochemistry of this compound was not established rigorously but is consistent with stereochemical outcomes for alkylations of other, related benzothiazines.
10. Harmata, M.; Kahraman, M. Synthesis 1994, 142.
11. Cary, J. M.; Moore, J. S.Org. Lett. 2002, 4, 4663.
12. Moore, J. S.; Weinstein, E. J.; Wu, Z. Tetrahedron Lett. 1991, 32, 2465.
13. Shi, L.; Narula, C. K.; Mak, K. T.; Kao, L.; Xu, Y.; Heck, R. F. J. Org. Chem. 1983, 48, 3894.
14. A 14% yield of the exocyclic alkene isomer of 7 was also produced. This isomerized to 7 in 82% yield upon column chromatography.
15. Cesati, R. R.; de Armas, J.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96.
16. Smidt, S. P.; Menges, F.; Pfaltz, A. Org. Lett. 2004, 6, 2023.
17. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
18. Ratio was 158:1 by GC.
19. Smith, A. B.; Schow, S. R.; Bloom, J. D.; Thompson, A. S.; Winzenberg, K. N. J. Am. Chem. Soc. 1982, 104, 4015.