Total synthesis of bengazole A

Organic Letters

Volumn 12, Issue 2, 2010, Pages 236-238

  Chandrasekhar, Srivari ^a   Sudhakar, Ambadi ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; BENGAZOLE A; OXAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; STEREOISOMERISM; SYNTHESIS;

ANTIFUNGAL AGENTS; MOLECULAR CONFORMATION; OXAZOLES; STEREOISOMERISM;

EID: 74949139942     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9024138     Document Type: Article

References (31)

1. Adamczeski, M.; Quiñoá, E.; Crews, P. J. Am. Chem. Soc. 1988, 110, 1598.
2. (a) Molinski, T. F. J. Nat. Prod. 1993, 56, 1.
3. (b) Antonio, J.; Molinski, T. F. J. Nat. Prod. 1993, 56, 54.
4. (a) Bugni, T. S.; Richards, B.; Bhoite, L.; Cimbora, D.; Harper, M. K.; Ireland, C. M. J. Nat. Prod. 2008, 71, 1095.
5. (b) Newman., D. J.; Cragg, G. M. J. Nat. Prod. 2007, 70, 461.
6. (c) Butler, M. S. J. Nat. Prod. 2004, 61, 2141.
7. (d) Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Chem. Rev. 2009, 109, 3012.
8. (e) Chandrasekhar, S.; Rambabu, C.; Reddy, A. S. Org. Lett. 2008, 10, 4355.
9. (f) Chandrasekhar, S.; Yaragorla, S. R.; Sreelakshmi, L. Tetrahedron Lett. 2007, 48, 7339.
10. Kolb, H. C.; Nieuwenhze, M. S. V.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
11. Chen, K. M.; Hardtmann, G. E.; Prasad, K.; Repic, O.; Shapiro, M. J. Tetrahedron Lett. 1987, 28, 155.
12. (a) Mulder, R. J.; Shafer, C. M.; Molinski, T. F. J. Org. Chem. 1999, 64, 4995.
13. (a) Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Angew. Chem., Int. Ed. 2006, 45, 6714.
14. (b) Bull, J. A.; Balskus, E. P.; Horan, R. A. J.; Langner, M.; Ley, S. V. Chem.-Eur. J. 2007, 13, 5515.
15. (a) Shafer, C. M.; Molinski, T. F. Tetrahedron Lett. 1998, 39, 2903.
16. (b) Chittari, P.; Hamada, Y.; Shioiri, T. Heterocycles 2000, 59, 465.
17. (c) Chittari, P.; Hamada, Y.; Shioiri, T. Synlett 1998, 1022.
18. Miller, R. A.; Smith, R. M.; Marcune, B. J. Org. Chem. 2005, 70, 9074.
19. R: 8.12 and 12.65 min.
20. Laïb, T.; Chastanet, J.; Zhu, J. J. Org. Chem. 1998, 63, 1709.
21. Omura, K.; Swern, D. Tetrahedron Lett. 1996, 37, 1651.
22. R: 5.8 and 8.8 min.
23. Pan, Q.; Zou, B.; Wang, Y.; Ma, D. Org. Lett. 2004, 6, 1009.
24. R: 6.6 and 8.4 min.
25. Rychnovsky, S. D.; Rogers, B. N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9.
26. 2 17a (exclusive product)
27. The unwanted isomer 19b was separated by column chromatography.
28. (a) Wipf, P.; Miller, C P. J. Org. Chem. 1993, 58, 3604.
29. (b) Wipf, P.; Lim. S. J. Am. Chem. Soc. 1995, 117, 558.
30. (c) Panek, J. S.; Beresis, R. T. J. Org. Chem. 1996, 61, 6496.
31. Kiyooka, S. Tetrahedron: Asymmetry 2003, 14, 2897.