Application of the Intramolecular Vinylogous Morita-Baylis-Hillman Reaction toward the Synthesis of the Spinosyn A Tricyclic Nucleus

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3157-3160

  Mergott, Dustin J ^a   Frank, Scott A ^a   Roush, William R ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; INSECTICIDE; MACROLIDE; SPINOSYN A; VINYL DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; SACCHAROPOLYSPORA; STEREOISOMERISM; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CYCLIZATION; INSECTICIDES; MACROLIDES; SACCHAROPOLYSPORA; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 0037026517     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026540d     Document Type: Article

References (26)

1. (a) Kirst, H. A.; Michel, K. H.; Martin, J. W.; Creemer, L. C.; Chio, E. H.; Yao, R. C.; Nakatsukasa, W. M.; Boeck, L.; Occolowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Jones, N. D.; Thompson, G. D. Tetrahedron Lett. 1991, 32, 4839.
2. (b) Kirst, H. A.; Michel, K. H.; Mynderase, J. S.; Chio, E. H.; Yao, R. C.; Nakatsukasa, W. M.; Boeck, L. D.; Occolowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Thompson, G. D. In Fermentation-Derived Tetracydic Macrolides; 1992; pp 214-225.
3. (c) Martynow, J. G.; Kirst, H. A. J. Org. Chem. 1994, 59, 1548.
4. (d) Sparks, T. C.; Crouse, G. D.; Durst, G. Pest Management Sci. 2001, 57, 896.
5. (e) Crouse, G. D.; Sparks, T. C.; Schoonover, J.; Gifford, J.; Dripps, J.; Bruce, T.; Larson, L. L.; Garlich, J.; Hatton, C.; Hill, R. L.; Worden, T. V.; Martynow, J. G. Pest Management Sci. 2001, 57, 177.
6. Dagani, R. Chem. Eng. News 1999, 77, July 5, p 30.
7. (a) Evans, D. A.; Black, W. C. J. Am. Chem. Soc. 1993, 115, 4497.
8. (b) Paquette, L. A.; Gao, Z. L.; Ni, Z. J.; Smith, G. F. J. Am. Chem. Soc. 1998, 120, 2543.
9. (c) Paquette, L. A.; Collado, I.; Purdie, M. J. Am. Chem. Soc. 1998, 120, 2553.
10. Frank, S. A.; Roush, W. R. J. Org. Chem. 2002, 67, 4316.
11. Kirst, H. A.; Michel, K. H.; Chio, E. H.; Yao, R. C.; Nakatsukasa, W. M.; Boeck, L.; Occolowitz, J. L.; Paschal, J. W.; Deeter, J. B.; Thompson, G. D. In Microbial Metabolites; Nash, C., Ed.; Wm. C. Brown: Dubuque, 1991; Vol. 32, p 109.
12. (a) Boeckman, R. K.; Barta, T. E. J. Org. Chem. 1985, 50, 3421.
13. (b) Roush, W. R.; Kageyama, M. Tetrahedron Lett. 1985, 26, 4327.
14. (c) Roush, W. R.; Kageyama, M.; Riva, R.; Brown, B. B.; Warmus, J. S.; Moriarty, K. J. J. Org. Chem. 1991, 56, 1192.
15. Wang, L. C.; Luis, A. L.; Agaplou, K.; Jang, H. Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402.
16. Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
17. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
18. Blanchette, M. A.; Choy, W.; Davis, J. T.; Essenfeld, A. P.; Masamune, S.; Roush, W. R.; Sakai, T. Tetrahedron Lett. 1984, 25, 2183.
19. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
20. (b) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
21. Roush, W. R.; Champoux, J. A.; Peterson, B. C. Tetrahedron Lett. 1996, 37, 8989.
22. Frank, S. A.; Chen, H.; Kunz, R. K.; Schnaderbeck, M. J.; Roush, W. R. Org. Lett. 2000, 2, 2691.
23. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
24. Hartwig, W. Tetrahedron 1983, 39, 2609.
25. (a) Ballestri, M.; Chatgilialoglu, C.; Clark, K. B.; Griller, D.; Giese, B.; Kopping, B. J. Org. Chem. 1991, 56, 678.
26. (b) Chatgilialoglu, C. Acc. Chem. Res. 1992, 25, 188.