Stereoselective Intramolecular Radical Addition of Polyhaloacetyl Functions to 2-Oxazolones. A Facile Synthesis of Statine and Its 2,2-Dichloro and 2,2-Difluoro Analogues

Journal of Organic Chemistry

Volumn 58, Issue 8, 1993, Pages 1997-1998

  Yamamoto, Takuya ^a   Ishibuchi, Seigo ^a   Ishizuka, Tadao ^a   Haratake, Mamoru ^a,b   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

^b Research Laboratories   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

STATINE; STATINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REACTION ANALYSIS;

EID: 0027204875     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00060a006     Document Type: Article

References (46)

1. Umezawa, H.; Aoyagi, T.; Morishima, H.; Matsuzaki, M.; Hamada, M.; Takeuchi, T. J. Antibiot. 1970, 23, 259.
2. Recent publication for statine synthesis: Kogen, H.; Nishi, T. J. Chem. Soc., Chem. Commun. 1987, 311.
3. Sakaitani, M.; Ohfune, Y. Tetrahedron Lett. 1987, 28, 3987.
4. Kano, S.; Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett 1987, 28, 6331.
5. Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141.
6. Harris, B. D.; Bhat, K. L.; Joullie, M. M. Tetrahedron Lett. 1987, 28, 2837.
7. Kano, S.; Yuasa, Y.; Yokomatsu, T.; Shibuya, S. J. Org. Chem. 1988, 53, 3865.
8. Nishi, T.; Kitamura, M.; Ohkuma, T.; Noyori, R. Tetrahedron Lett 1988, 29, 6327.
9. Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368.
10. Takahata, H.; Yamazaki, K.; Takamatsu, T.; Yamazaki, T.; Momose, T. J. Org. Chem. 1990, 55, 3947.
11. Woo, P. W. K. Tetrahedron Lett. 1985, 26, 2973.
12. Dufour, M. N.; Juoin, P.; Poncet, J.; Pontaroni, A.; Castro, B. J. Chem. Soc. Perkin Trans. 1 1986, 1895.
13. Mulzer, J.; Büttelmann, B.; Münch, W. Liebigs Ann. Chem. 1988, 445.
14. Rittle, K. E.; Homnick, C. F.; Ponticello, G. S.; Evans, B. E. J. Org. Chem. 1982, 47, 3016.
15. Hollaway, M. W.; Salituro, F. G.; Rich, D. H. J. Med. Chem. 1987, 30, 374.
16. Danishefsky, S.; Kobayashi, S.; Keerwin, J. F., Jr. J. Org. Chem. 1982, 47, 1981.
17. Schostarez, H. J. J. Org. Chem. 1988, 53, 3628.
18. Steulemann, R.; Klostermeyer, H. Liebigs Ann. Chem. 1975, 2445.
19. Kinoshita, M.; Hagiwara, A.; Aburaki, S. Bull. Chem. Soc. Jpn. 1975, 48, 570.
20. Liu, W. S.; Glover, G. I. J. Org. Chem. 1978, 43, 754.
21. Takemoto, Y.; Matsumoto, T.; Ito, Y.; Terashima, S. Tetrahedron Lett. 1990, 31, 217.
22. Misiti, D.; Zappia, G. Tetrahedron Lett. 1990, 31, 7359.
23. Ohta, T.; Shiokawa, S.; Sakamoto, T.; Nozoe, S. Tetrahedron Lett. 1990, 31, 7329.
24. Koot, W.-J.; Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. M. Tetrahedron Lett. 1991, 32, 401.
25. Iizuka, K.; Kamijo, T.; Harada, H.; Akahane, K.; Kubota, T.; Etoh, Y.; Shimaoka, I.; Tsubaki, A.; Murakami, M.; Yamaguchi, T.; Iyobe, A.; Umeyama, H.; Kiso, Y. Chem. Pharm. Bull. 1990, 38, 2487.
26. Repine, J. T.; Himmelsbach, R. J.; Hodges, J. C.; Kaltenbronn, J. S.; Sircar, I.; Skeean, R. W.; Brennan, S. T.; Hurley, T. R.; Lunney, E.; Humblet, C. C.; Weishaar, R. E.; Rapundalo, S.; Ryan, M. J.; Taylor, D. G., Jr.; Olson, S. C.; Michniewicz, B. M.; Romberg, B. E.; Belmont, D. T.; Taylor, M. D. J. Med. Chem. 1991, 34, 1935.
27. Raddatz, P.; Jonczyk, A.; Minck, K.-O.; Rippmann, F.; Schittenhelm, C.; Schmitges, C. J. J. Med. Chem. 1992, 35, 3525.
28. Thaisrivongs, S.; Pals, D. T.; Kati, W. M.; Turner, S. R.; Thomasco, L. M.; Watt, W. J. Med. Chem. 1986, 29, 2080.
29. Thaisrivongs, S.; Schostarez, H. J.; Pals, D. T.; Turner, S. R. J. Med. Chem. 1987, 30, 1837.
30. Altenburger, J. M.; Schirlin, D. Tetrahedron Lett. 1991, 32, 7255.
31. Hong, W.; Dong, L.; Cai, Z.; Titmas, R. Tetrahedron Lett. 1992, 33, 741.
32. 2,2-Difluoro-3-hydroxy-4-aminocarboxyl derivatives can be oxidized to 2,2-difluoro-3-oxo-4-aminocarboxyl derivatives, an important class of interleukin-1β converting enzyme inhibitors: Robinson, R. P.; Donahue, K. M. J. Org. Chem. 1992, 57, 7309 and references cited therein.
33. Kunieda, T.; Ishizuka, T.; Higuchi, T.; Hirobe, M. J. Org. Chem. 1988, 53, 3381.
34. Ishizuka, T.; Ishibuchi, S.; Kunieda, T. Tetrahedron Lett. 1989, 30, 3449.
35. Matsumoto, H.; Nakano, T.; Nagai, Y. Tetrahedron Lett. 1973, 5143.
36. Matsumoto, H.; Nakaido, T.; Nagai, Y. Tetrahedron Lett. 1975, 899.
37. Matsumoto, H.; Nikaido, T.; Nagai, Y. J. Org. Chem. 1976, 41, 396.
38. Matsumoto, H.; Nakano, T.; Ohkawa, K.; Nagai, Y. Chem. Lett. 1978, 363.
39. Matsumoto, H.; Nakano, T.; Takasu, K.; Nagai, Y. J. Org. Chem. 1978, 43, 1734.
40. Nakano, T.; Shimada, Y.; Sako, R.; Kamiya, M.; Matsumoto, H.; Nagai, Y. J. Org. Chem. 1982, 1255.
41. Damon, R. E.; Coppola, G. M. Tetrahedron Lett. 1990, 31, 2849.
42. Evans, D. A.; Britton, T. C.; Ellman, J. A. Tetrahedron Lett. 1987, 28, 6141.
43. Matsunaga, H.; Kimura, K.; Ishizuka, T.; Haratake, M.; Kunieda, T. Tetrahedron Lett. 1991, 32, 7715.
44. Matsunaga, H.; Ishizuka, T.; Marubayashi, N.; Kunieda, T. Chem. Pharm. Bull. 1992, 40, 1077.
45. Ishibuchi, S.; Ikematsu, Y.; Ishizuka, T.; Kunieda, T. Tetrahedron Lett. 1991, 32, 3523.
46. 4.5, = 4.5 Hz, H-5): Sham, H. L.; Rempel, C. A.; Stein, H.; Cohen, J. J. Chem. Soc., Chem. Commun. 1990, 904.