Synthesis of 6-deoxyerythronolide B. Implementation of a general strategy for the synthesis of macrolide antibiotics

Tetrahedron Letters

Volumn 38, Issue 1, 1997, Pages 53-56

  Evans, David A ^a   Kim, Annette S ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0031034280     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02258-7     Document Type: Article

References (27)

1. Nakayama, I. In Macrolide Antibiotics. Chemistry, Biology, and Practice; Omura, S., Ed.; Academic Press: Orlando FL, 1984; pp 261-298.
2. 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, 281-283.
3. (a) Cortes, J.; Haydock, S. F.; Roberts, G. A.; Bevitt, D. J.; Leadlay, P. F. Nature 1990, 348, 176-178.
4. (b) Donadio, S.; Staver, M. J.; McAlpine, J. B.; Swanson, S. J.; Katz, L. Science 1991, 252, 675-679.
5. (c) Malpartida, F.; Hopwood, D. A. Nature 1984, 309, 462-464.
6. (a) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
7. (b) Evans, D. A.; Ng, H. P.; Clark, J. S.; Rieger, D. L. Tetrahedron 1992, 48, 2127-2142.
8. Masamune, S.; Hirama, M.; Mori, S.; Ali, S. A.; Garvey, D. S. J. Am. Chem Soc. 1981, 103, 1568-1571.
9. 7 carbonyl. A preponderance of data had documented the formation of this array in double stereodifferentiating reactions of both (Z) and (E) metal enolates. See: (a) Evans, D. A.; Dart, M. J.; Duffy, J. L.; Rieger, D. L. J. Am. Chem. Soc. 1995, 117, 9073-9074.
10. 5 and this reversal of enolate facial bias (eq 3,4). equation presented.
11. These preliminary studies employed ToCl4 as the catalyst. Evans, D.A.; Dart, M.J. Unpublished Results.
12. Evans, D. A.; Yang, M. G.; Dart, M. J.; Duffy, J. L.; Kim, A. S. J. Am. Chem. Soc. 1995, 117, 9598-9599.
13. Ng, H. P. Ph.D. Thesis, Harvard University, Aug. 1993.
14. Oishi, T.; Nakata, T. Acc. Chem. Res. 1984, 17, 338-344.
15. Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487-2489.
16. Evans, D. A.; Chapman, K. T.; Carreira, E. M. J. Am. Chem. Soc. 1988, 110, 3560-3578.
17. Masamune, S.; Ellingboe, J. W.; Choy, W. J. Am. Chem. Soc. 1982, 104, 5526-5528.
18. Woodward, R. B. et al. J. Am. Chem. Soc. 1981, 103, 3213-3215.
19. (a) Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. Tetrahedron 1990, 46, 4613-4628.
20. (b) Yonemitsu, O. J. Synth. Org. Chem., Jpn. 1994, 52, 74-83.
21. (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 11975, 1574-1585.
22. (b) Barton, D. H. R.; Dorchak, J.; Jaszberenyi, J. Cs. Tetrahedron 1992, 48, 7435-7446.
23. (a) Hikota, M.; Sakurai, Y.; Horita, K.; Yonemitsu, O. Tetrahedron Lett. 1990, 31, 6367-6370.
24. (b) Hikota, M.; Tone, H.; Horita, K.; Yonemitsu, O. J. Org. Chem. 1990, 55, 7-9.
25. (c) Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
26. Corey, E. J.; Melvin, L. S. Tetrahedron Lett. 1975, 929-932.
27. Corey, E. J.; Kim, S.; Yoo, S.; Nicolaou, K. C.; Melvin, L. S.; Brunelle, D. J.; Falck, J. R.; Trybulski, E. J.; Lett, R.; Sheldrake, P. W. J. Am. Chem. Soc. 1978, 100, 4620-4622.