Synthesis of an enantiomerically pure serine-derived thiazole

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7671-7676

  Sowinski, Jennifer A ^a   Toogood, Peter L ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029796221     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961408a     Document Type: Article

References (34)

1. For leading reference, see: Davidson, B. S. Chem. Rev. 1993, 93, 1771.
2. Pettit, G. R.; Kamano, Y.; Heralk, C. L.; Tuinman, A. A.; Boettner, F. E.; Kizu, H.; Schmidt, U.; Baczynskyj, L.; Tomer, K. B.; Boetems, R. J. J. Am. Chem. Soc. 1987, 109, 6883.
3. Foster, M. P.; Concepcion, G. P.; Caraan, G. B.; Ireland, C. M. J. Org. Chem. 1992, 57, 6671.
4. Northcote, P. T.; Blunt, J. W.; Munro, W. M. G. Tetrahedron Lett. 1991, 32, 6411.
5. Ireland, C.; Scheuer, P. J. J. Am. Chem. Soc. 1980, 102, 5688.
6. For recent examples, see: (a) Kelly, R. C.; Gebhard, I.; Wicnienski, N. J. Org. Chem. 1986, 51, 4590.
7. (b) Schmidt, U.; Utz, R.; Lieberknecht, A.; Griesser, H.; Potzolli, B.; Bahr, J.; Wagner, K.; Fischer, P. Synthesis 1987, 233.
8. (c) Bredenkamp, M. W.; Holzapfel, C. W.; van Zyl, W. J. Synth. Commun. 1990, 20, 2235.
9. (d) Hamada, Y.; Hayashi, K.; Shioiri, T. Tetrahedron Lett. 1991, 32, 931.
10. (e) Pattenden, G.; Thom, S. M. J. Chem. Soc., Perkin Trans, 1 1993, 1629.
11. (f) Martin, B. J.; Clough, J. M.; Pattenden, G.; Waldron, I. R. Tetrahedron Lett. 1993, 34, 5151.
12. Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.; Shioiri, T. J. Org. Chem. 1987, 52, 1252.
13. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744. Burgess reagent is commercially available from Aldrich and Fluka.
14. Wipf, P.; Fritch, P. C. Tetrahedron Lett. 1994, 35, 5397.
15. Itagaki, F.; Shigemori, H.; Ishibashi, M.; Nakamura, T.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 5540.
16. Kobayashi, J.; Itagaki, F.; Shigemori, H.; Takao, T.; Shimonishi, Y. Tetrahedron 1995, 51, 2525.
17. Sowinski, J. A.; Toogood, P. L. Tetrahedron Lett. 1995, 36, 67.
18. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
19. Meyers, A. I.; Aguilar, E. Tetrahedron Lett. 1994, 35, 2473.
20. Bredenkamp, M. W.; Holzapfel, C. W.; Snyman, R. M.; van Zyl, W. J. Synth. Commun. 1992, 22, 3029.
21. Schmidt, U.; Gleich, P.; Griesser, H.; Utz, R. Synthesis 1986, 992.
22. Commercially available from Bachern (California).
23. Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 6267.
24. Clausen, K.; Thorsen, M.; Lawesson, S. O.; Spatola, A. F. J. Chem. Soc., Perkin Trans. 1 1984, 785. Lawesson's reagent is commercially available from Sigma and Aldrich.
25. (a) Bajgrowicz, J. A.; El Hallaoui, A.; Jacquier, R.; Pigiere, Ch.; Viallefont, Ph. Tetrahedron 1985, 41, 1833.
26. (b) Photaki, I. J. Am. Chem. Soc. 1963, 85, 1123.
27. (a) Cheung, S. T.; Benoiton, N. L. J. Can. Chem. 1977, 55, 906.
28. (b) Olsen, R. K. J. Org. Chem. 1970, 35, 1912.
29. Wojciechowska, H.; Pawlowicz, R.; Andruszkiewiez, R.; Grzybowska, J. Tetrahedron Lett. 1978, 4063.
30. Cherney, R. J.; Wang, L. J. Org. Chem. 1996, 61, 2544.
31. Christie, B. D.; Rapoport, H. J. Org. Chem. 1985, 50, 1239.
32. Guthrie, R. D.; Nicolas, E. C. J. Am. Chem. Soc. 1981, 103, 4638.
33. Barlos, K.; Papaioznnou, D.; Cordopatis, P.; Theodoropoulos, D. Tetrahedron 1983, 39, 475.
34. Attempts to form the thioamide from N-Tr-O-methyl-L-serinamtde were unsuccessful. The polarity of the primary thioamide formed prohibited its separation from decomposition products; consequently, the Hantzsch method was not investigated using the N-trityl protecting group.