Methodology for the synthesis of substituted 1,3-oxazoles

Synlett

Volumn , Issue 4, 2010, Pages 591-594

  Williams, David R ^a   Fu, Liangfeng ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

Alkylation; Halogen dance rearrangement; Oxazoles

Indexed keywords

1,3 OXAZOLE DERIVATIVE; LITHIUM; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ZINC;

ALKYLATION; ARTICLE; ARYLATION; CROSS COUPLING REACTION; ISOMERIZATION; NEGISHI REACTION;

EID: 77953905163     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/S-0029-1219374     Document Type: Article

References (33)

1. Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. J. Am. Chem. Soc. 1991, 113, 3173.
2. Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995, 117, 8126.
3. For structure revision of diazonamide A, see: Li, J.; Burgett, A. W. G.; Esser, L.; Amezcua, C.; Harran, P. G. Angew. Chem. Int. Ed. 2001, 40, 4770.
4. (a) Hagelueken, G.; Albrecht, S. C.; Steinmetz, H.; Jansen, R.; Heinz, D. W.; Kalesse, M.; Schubert, W.-D. Angew. Chem. Int. Ed. 2008, 48, 595.
5. (b) For the recent isolation of hemiphorboxazole A: Dalisay, D. S.; Molinski, T. F. Org. Lett. 2009, 11, 1967.
6. Shinya, K.; Wierzba, K.; Matsuo, K.; Ohtani, T.; Yamada, Y.; Furihata, K.; Hayakawa, Y.; Seto, H. J. Am. Chem. Soc. 2001, 123, 1262.
7. (a) Rosener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846.
8. (b) Dalisay, D. S.; Rogers, E. W.; Edison, A. S.; Molinski, T. F. J. Nat. Prod. 2009, 72, 732.
9. For examples, see: (a) Kanoh, K.; Matsuo, Y.; Adachi, K.; Imagawa, H.; Nishizawa, M.; Shizuri, Y. J. Antibiot. 2005, 58, 289.
10. (b) Perez, L. J.; Faulkner, D. J. J. Nat. Prod. 2003, 66, 247.
11. (c) Kohno, J.; Kameda, N.; Nisho, M.; Kinumaki, A.; Komatsubara, S. J. Antibiot. 1996, 49, 1063.
12. (a) Phillips, A. J.; Uto, Y.; Wipf, P.; Reno, M. J.; Williams, D. R. Org. Lett. 2000, 2, 1165.
13. (b) For the initial application of this methodology in the synthesis of hennoxazole A, see: Williams, D. R.; Brooks, D. A.; Berliner, M. A. J. Am. Chem. Soc. 1999, 121, 1303.
14. (a) Besselievre, F.; Piguel, S.; Mahuteau-Betzer, F.; Grierson, D. S. Org. Lett. 2008, 10, 4029.
15. (b) Flegeau, E. F.; Popkin, M. E.; Greaney, M. F. Org. Lett. 2008, 10, 2717.
16. (c) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 2905.
17. (d) Smith, A. B. III.; Minbiole, K. P.; Freeze, S. Synlett 2001, 1739.
18. Hammerle, J.; Spina, M.; Schnurch, M.; Mihovilovic, M. D.; Stanetty, P. Synthesis 2008, 3099.
19. For leading references, see: (a) Vedejs, E.; Luchetta, L. M. J. Org. Chem. 1999, 64, 1011.
20. (b) Whitney, S. E.; Rickborn, B. J. Org. Chem. 1991, 56, 3058.
21. Williams, D. R.; McClymont, E. L. Tetrahedron Lett. 1993, 34, 7705.
22. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem. Int. Ed. 2004, 43, 2206.
23. Williams, D. R.; Brooks, D. A.; Meyer, K. G. Tetrahedron Lett. 1998, 39, 8023.
24. Meyers, A. I.; Lawson, J. P. Tetrahedron Lett. 1981, 22, 3163.
25. (a) Lee, K.; Counceller, C. M.; Stambuli, J. P. Org. Lett. 2009, 11, 1457.
26. (b) Williams, D. R.; Fu, L. Org. Lett. 2010, 12, DOI: 10.1021/ol902833p.
27. For reviews of the halogen dance reaction, see: (a) Bunnett, J. F. Acc. Chem. Res. 1972, 5, 139.
28. (b) Marzi, E.; Bigi, A.; Schlosser, M. Eur. J. Org. Chem. 2001, 1371.
29. For a leading reference, see: Stanetty, P.; Schnurch, M.; Mereiter, K.; Mihovilovic, M. D. J. Org. Chem. 2005, 70, 567.
30. Strangeland, E. L.; Sammakia, T. J. Org. Chem. 2004, 69, 2381.
31. Stanetty, P.; Spina, M.; Mihovilovic, M. D. Synlett 2005, 1433.
32. 4. Evaporation of solvent and flash silica gel chromatography (8:1 hexane-EtOAc) provided 5-bromo-2-phenylthio-1,3-oxazole (75% yield).
33. 13C NMR spectroscopy, IR spectroscopy, and HRMS analysis.