Formal synthesis of 6-deoxyerythronolide B

Organic Letters

Volumn 8, Issue 10, 2006, Pages 2191-2194

  Crimmins, Michael T ^a   Slade, David J ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 DEOXYERYTHRONOLIDE B; 6-DEOXYERYTHRONOLIDE B; ALDEHYDE; DRUG DERIVATIVE; ERYTHROMYCIN; PROPIONALDEHYDE; THIAZOLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALDEHYDES; ERYTHROMYCIN; MOLECULAR STRUCTURE; THIAZOLIDINES;

EID: 33744750200     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0607241     Document Type: Article

References (26)

1. McGuire, J. M.; Bunch, R. L.; Anderson, R. C.; Boaz, H. E.; Flynn, E. H.; Powell, H. M.; Smith, J. W. Antibiot. Chemother. 1952, 2, 281.
2. Nakayama, I. In Macrolide Antibiotics. Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: Orlando, FL, 1984; p 261.
3. (a) Cortes, J.; Haydock, S. F.; Roberts, G. A.; Bevitt, D. J.; Leadlay, P. F. Nature 1990, 348, 176.
4. (b) Donadio, S.; Staver, M. J.; McAlpine, J. B.; Swanson, S. J.; Katz, L. Science 1991, 252, 675.
5. (c) Malpartida, F.; Hopwood, D. A. Nature 1984, 309, 462.
6. Martin, J. R.; Rosenbrook, W. Biochemistry 1967, 6, 435.
7. Staunton, J.; Wilkinson B. Chem. Rev. 1997, 97, 2611.
8. (a) Kaneda, T.; Butte, J. C.; Taubman, S. B.; Corcoran, J. W. J. Biol. Chem. 1962, 237, 322.
9. (b) Cane, D. E.; Hasler, H.; Liang, T. J. Am. Chem. Soc. 1981, 103, 5960.
10. (c) Cane, D. E.; Yang, C.-C. J. J. Am. Chem. Soc. 1987, 109, 1255.
11. (d) Cane, D. E.; Prabhakaran, P. C.; Tan, W.; Ott, W. R. Tetrahedron Lett. 1991, 32, 5457.
12. (e) Yue, S.; Duncan, J. S.; Yamamoto, Y.; Hutchinson, C. R. J. Am. Chem. Soc. 1987, 109, 1253.
13. (a) Evans, D. A.; Kim, A. S.; Metternich, R.; Novack, V. J. J. Am. Chem. Soc. 1998, 120, 5921.
14. (b) Myles, D. C.; Danishefsky, S. J.; Schulte, G. J. Org. Chem. 1990, 55, 1636.
15. (c) Masamune, S.; Hirama, M.; Mori, S.; Ali, S. A.; Garvey, D. S. J. Am. Chem. Soc. 1981, 103, 1568.
16. (a) Crimmins, M. T.; Chaudhary, K. Org. Lett. 2000, 2, 775.
17. (b) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
18. (a) Crimmins, M. T.; Christie, H. S.; Chaudhary, K.; Long, A. J. Am. Chem. Soc. 2005, 127, 13810.
19. (b) Crimmins, M. T.; Caussanel, F. J. Am. Chem. Soc. 2006, 129, 3128.
20. Sano, S.; Kobayashi, Y.; Kondo, T.; Takebayashi, M.; Maruyama, S.; Fujita, T.; Nagao, Y. Tetrahedron Lett. 1995, 36, 2097.
21. Still, W. C.; Gennari, C. Tetrahedron Lett. 1983, 24, 4405.
22. Myers, A. G.; Yang, B. H.; Chen, H.; McKinstry, L.; Kopecky, D. L.; Gleason, J. L. J. Am. Chem. Soc. 1997, 119, 6496.
23. Myers, A. G.; Yang, B. H.; Kopecky, D. J. Tetrahedron Lett. 1996, 37, 3623.
24. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
25. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
26. (b) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.