Highly chemoselective trichloroacetimidate-mediated alkylation of ascomycin: A convergent, practical synthesis of the immunosuppressant L- 733,725

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 1859-1867

  Song, Zhiguo ^a   DeMarco, Anthony ^a   Zhao, Mangzhu ^a   Corley, Edward G ^a   Thompson, Andrew S ^a   McNamara, James ^a   Li, Yulan ^a   Rieger, Dale ^a   Sohar, Paul ^a   Mathre, David J ^a   Tschaen, David M ^a   Reamer, Robert A ^a   Huntington, Martha F ^a   Ho, Guo Jie ^a   Tsay, Fuh Rong ^a   Emerson, Khateeta ^a   Shuman, Richard ^a   Grabowski, Edward J J ^a   Reider, Paul J ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; ASCOMYCIN; FLUOROMETHANE; IMIDAZOLE DERIVATIVE; IMMUNOSUPPRESSIVE AGENT; L 733725; SOLVENT; TACROLIMUS; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CRYSTALLIZATION; DRUG PURIFICATION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE;

EID: 0033583152     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981805g     Document Type: Article

References (33)

1. (a) Goulet, M.; McAlpine, S. R.; Staruch, M. J.; Koprak, S.; Dumont, F. J.; Cryan, J. G.; Wiederrech, G. J.; Rosa, R.; Wilusz, M. B.; Peterson, L. B.; Wyvratt, M. J.; Parsons, W. H. Bioorg. Med. Chem. Lett. 1998, 8, 2253.
2. (b) Goulet, M.; Sinclair, P. J.; Wong, F.; Wyvratt, M. J. US Patent 5247076, 1993.
3. (c) Kawai, M.; Gunawardana, I. W. K.; Mollison, K. W.; Hsieh, G. C.; Lane, B. C.; Luly, J. R. Biiorg. Med. Chem. Lett. 1998, 8, 935.
4. (d) Wagner, R.; Rhodes, T. A.; Ore, Y. S.; Lane, B. C.; Hsieh, G.; Mollison, K. W.; Luly, J. R. J. Med. Chem. 1998, 41, 1764.
5. (e) Goulet, M. T.; Rupprecht, K. M.; Sinclair, P. J.; Wyvratt, M. J.; Parsons, W. H. Perspect. Drug Discovery Des. 1994, 2, 145.
6. (f) Van Duyne, G. D.; Standaert, R. F.; Karplus, P. A.; Schreiber, S. L.; Clardy, J. Science 1991, 252, 839.
7. (a) Jones, T.; Reamer, R. A., Desmond, R.; Mills, S. G. J. Am. Chem. Soc. 1990, 112, 2998.
8. (b) Byrne, K. M., Shafiee, A.; Nielsen, J. B., Arison, B.; Monaghan, R. L.; Kaplan, L. In Microbial Metabolites; Nash, C., Hunter-Cevera, J., Cooper, R., Eveleigh, D. E., Hamill, R., Eds.; Wm. C. Brown Publishers: Dubuque, IA, 1992; Vol. 32, p 29.
9. (a) Grimmett, M. R. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Potte, K. T., Eds.; Pergamon Press: New York, 1984; Vol. 5, pp 457-497.
10. (b) Sigehara, I.; Nakajima, T.; Nishimura, S.; Ohshima, T. EP 365030A1, 1989.
11. (c) Walia, J. S.; Walia, A. S.; Lankin, D. C., Petterson, R. C.; Singh, J. J. Heterocycl. Chem. 1985, 22, 1117.
12. (a) Mikol, G. J.; Russel, G. A. Organic Syntheses; Wiley: New York, 1963; Collect, Vol. IV, p 937.
13. (b) Riley, H. A.; Gray, A. R. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. II, p 509.
14. (c) Desmond, R.; Mills, S.; Volante, R. P., Shinkai, I. Synth. Commun. 1989, 19, 379.
15. (d) Keifanto, M. M.; Delepine, M. M. Compt. Rend. 1962, 254, 493.
16. (e) Floyd, M. B.; Du, M. T.; Fabio, P. F.; Jacob, L. A.; Johnson, B. D. J. Org. Chem. 1985, 50, 5022.
17. (a) Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett. 1988, 33, 4139.
18. (b) Schmidt, U.; Respondek, M.; Liebernecht, A.; Werner, J.; Fisher, P. Synthesis 1989, 256.
19. (a) Brown, R. S.; Manoharan, T. S. J. Org. Chem. 1988, 53, 1107.
20. (b) Brown, R. S. Ulan, J. G. J. Am. Chem. Soc. 1983, 105, 2382.
21. (c) Brown, R. S.; Curtis, N. J. J. Org. Chem. 1980, 45, 4038.
22. (d) Wu, D. C. J.; Cheer, C. J.; Panzica, R. P.; Abushannab, E. J. Org. Chem. 1982, 47, 2661.
23. (e) Hamamichi, N.; Migasaka, T. Tetrahedron Lett. 1985, 26, 4743.
24. (a) Bell, A. S.; Roberts, D. A.; Ruddock, K. S. Tetrahedron Lett. 1988, 29, 5013.
25. (b) Sekaiya, A.; Ishikawa, N. Organomet. Chem. 1977, 125, 281.
26. (c) Tamao, K.; Sumitani, K.; Zembayashi, M.; Fujioka, A.; Kodama, S.; Nakajima, I.; Minato, A.; Kumada, M. Bull. Chem. Soc. Jpn. 1976, 49, 1958.
27. (f) Kalinin, V. N. Synthesis 1992, 413.
28. Mann, I. S.; Widdowson, D. A. Tetrahedron 1991, 47, 7981.
29. (a) Bolton, J. L.; McClelland, R. A. Can. J. Chem. 1989, 67, 1139.
30. (b) Freedman, H. H. In Carbonium Ions; Olah, G. A., Schleyer, P. von R., Eds.; Wiley-Interscience: New York, 1973; Vol. IV, pp 1501-1678.
31. 2 (23, 2.0). (a) Riddick, J. A. Organic Solvents: Physical Properties and Methods of Purification; Wiley: New York, 1986; p 536.
32. 2 from Merck Index 1989; p 9160).
33. Julia, M.; Mestdagh, H. Tetrahedron 1983, 39, 433.