Ring-opening of oxazolines derived from l-serine: a short and efficient stereoselective synthesis of all four diastereomers of 3-mercaptoaspartic acid derivatives

Tetrahedron Letters

Volumn 48, Issue 41, 2007, Pages 7309-7312

  Lee, Sang Hyeup ^a,b   Bok, Juhan ^a   Qi, Xin ^c   Kim, Sook Kyung ^c   Lee, Yoon Sik ^d   Yoon, Juyoung ^c  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

^b Catholic University of Daegu   (South Korea)

^c Ewha Womans University   (South Korea)

^d Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

3 MERCAPTOASPARTIC ACID DERIVATIVE; ASPARTIC ACID; ASPARTIC ACID DERIVATIVE; OXAZOLINE 4,5DICARBOXYLATE; OXAZOLINE DERIVATIVE; SERINE; THIOACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER; STEREOCHEMISTRY;

EID: 34548500781     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.041     Document Type: Article

References (49)

1. For some recent reviews, see: Chan, W. C., Higton, A., Davies, J. S. In Amino Acids, Peptides and Proteins, 2006; pp 1-73.
2. Ager D.J., and Fotheringham I.G. Curr. Opin. Drug Discov. Dev. 4 (2001) 800
3. Asymmetric Synthesis of Novel Sterically Constrained Amino Acids; Symposium-in-Print, Hruby, V. J., Soloshonok, V. A. Eds., Tetrahedron 2001, Vol. 57, p 6329 and references cited therein.
4. Lee K.-H. Curr. Pharm. Des. 8 (2002) 795
5. Bouifraden S., Drouot C., El Hadrami M., Guenoun F., Lecointe L., Mai N., Paris M., Pothion C., Sadoune M., Sauvagnat B., Amblard M., Aubagnac J.L., Calmes M., Chevallet P., Daunis J., Enjalbal C., Fehrentz J.A., Lamaty F., Lavergne J.P., Lazaro R., Rolland V., Roumestant M.L., Viallefont P., Vidal Y., and Martinez J. Amino Acids 16 (1999) 345
6. Ohfune Y. Acc. Chem. Res. 25 (1992) 360
7. Fernandez-Megia E., Paz M.M., and Sardina F.J. J. Org. Chem. 59 (1994) 7643 and references cited therein
8. Charvillon F.B., and Amouroux R. Synth. Commun. 27 (1997) 395
9. Shibata N., Baldwin J.E., Jacobs A., and Wood W.E. Tetrahedron 52 (1996) 12839-12852
10. Shibata N., Baldwin J.E., Jacobs A., and Wood W.E. Synlett 1996 (1996) 519
11. Antolini L., Bucciarelli M., Caselli E., Davoli P., Forni A., Moretti I., Prati F., and Torre G. J. Org. Chem. 62 (1997) 8784
12. Gordon E.M., Godfrey J.D., Delaney N.G., Asaad M.M., Langen D.V., and Cushman D.W. J. Med. Chem. 31 (1988) 2199
13. For some recent examples, see:. Bischoff L., David C., Martin L., Meudal H., Roques B.P., and Fournié-Zaluski M.-C. J. Org. Chem. 62 (1997) 4848
14. David C., Bischoff L., Meudal H., Mothé A., Mota N.D., DaNascimento S., Llorens-Cortès C., Fournié-Zaluski M.-C., and Roques B.P. J. Med. Chem. 42 (1999) 5197
15. David C., Bischoff L., Roques B.P., and Fournié-Zaluski M.-C. Tetrahedron 56 (2000) 209
16. Martin L., Cornille F., Coric P., Roques B.P., and Fournié-Zaluski M.-C. J. Med. Chem. 41 (1998) 3450
17. Gaucher J.F., Selkti M., Tiraboschi G., Prangé T., Roques B.P., Tomas A., and Fournié-Zaluski M.-C. Biochemistry 38 (1999) 12569
18. Robl J.A., Sulsky R., Sieber-McMaster E., Ryono D.E., Cimarusti M.P., Simpkins L.M., Karanewsky D.S., Chao S., Asaad M.M., Seymour A.A., Fox M., Smith P.L., and Trippodo N.C. J. Med. Chem. 42 (1999) 305
19. Baxter A.D., Bhogal R., Bird J.B., Buckley G.M., Gregory D.S., Hedger P.C., Manallack D.T., Massil T., Minton K.J., Montana J.G., Neidle S., Owen D.A., and Watson R.J. Bioorg. Med. Chem. Lett. 7 (1997) 2765
20. Akasaka K., Akamatsu H., Kimoto Y., Komatsu Y., Shimizu T., Shimomura N., Tagami K., and Negi S. Chem. Pharm. Bull. 47 (1999) 1525
21. Akasaka K., Komatsu Y., Tagami K., Shimizu T., Shimomura N., Naka H., Hayashi K., and Negi S. Chem. Pharm. Bull. 47 (1999) 1532
22. Blommaert A., Turcaud S., Anne C., and Roques B.P. Bioorg. Med. Chem. Lett. 12 (2004) 3055
23. Sukonpan C., Oost T., Goodnough M., Tepp W., Johnson E.A., and Rich D.H. J. Pept. Res. 63 (2004) 181
24. For some recent examples, see:. Cardillo G., Glentilucci L., and Tolomelli A. Aldrichim. Acta 36 (2003) 39 and references cited therein
25. Feske B.D., Kaluzna I.A., and Stewart J.D. J. Org. Chem. 70 (2005) 9654
26. Voronkov M.V., Gontcharov A.V., Wang Z.-M., Richardson P.F., and Kolb H.C. Tetrahedron 60 (2004) 9043
27. García Ruano J.L., and García Paredes C. Tetrahedron Lett. 41 (2000) 5357
28. Lee S.-H., Yoon J., Nakamura K., and Lee Y.-S. Org. Lett. 2 (2000) 1243
29. Lee S.-H., Yoon J., Chung S.-H., and Lee Y.-S. Tetrahedron 57 (2001) 2139
30. Lee S.-H., Qi X., Yoon J., Nakamura K., and Lee Y.-S. Tetrahedron 58 (2002) 2777
31. Qi X., Lee S.-H., Yoon J., and Lee Y.-S. Tetrahedron 59 (2003) 7409
32. Qi X., Lee S.-H., Yoon J., and Lee Y.-S. Tetrahedron 60 (2004) 3599
33. Qi X., Lee S.-H., Yoon J., and Lee Y.-S. Tetrahedron 60 (2004) 4133
34. Cardillo G., Gentilucci L., Tolomelli A., and Tomasini C. Synlett (1999) 1727
35. 5 = 264.0872. (4R,5S)-13 shows same spectral data and optical rotation with opposite sign compared with (4S,5R)-9.
36. 1 = 340.0855. d-threo-(2S,3R)-14 shows same spectral data and optical rotation with opposite sign compared with l-threo-10.
37. De Angelis M., and Campiani G. Tetrahedron Lett. 45 (2004) 2355
38. Suga H., Ikai K., and Ibata T. J. Org. Chem. 64 (1999) 7040
39. Suga H., Ikai K., and Ibata T. Tetrahedron Lett. 39 (1998) 869
40. Evans D.A., Janey J.M., Magomedov N., and Tedrow J.S. Angew. Chem., Int. Ed. 40 (2001) 1884
41. Stereochemical interconversion of vicinal aminoalochols via the formation of intermediate oxazoline is well documented. For examples, of β-amino-α-hydroxy esters accompanying C-α inversion via oxazoline-5-carboxylates, see:. Sakakura A., Kondo R., and Ishihara K. Org. Lett. 7 (2005) 1971 and references cited therein
42. Singh O.V., and Han H. Tetrahedron Lett. 44 (2003) 5289
43. Phillips A.J., Uto Y., Wipf P., Reno M.J., and Williams D.R. Org. Lett. 2 (2000) 1165 and references cited therein
44. For examples of β-hydroxy-α-amino esters accompanying C-β inversion via oxazoline-4-carboxylates, see:. Tosaki S.-y., Tsuji R., Ohshima T., and Shibasaki M. J. Am. Chem. Soc. 127 (2005) 2147
45. Castagnolo D., Armaroli S., Corelli F., and Botta M. Tetrahedron: Asymmetry 15 (2004) 941
46. Hamamoto H., Mamedov V.A., Kitamoto M., Hayashi N., and Tsuboi S. Tetrahedron: Asymmetry (2000) 4485
47. Lee J.-M., Lim H.-S., Seo K.-C., and Chung S.-K. Tetrahedron: Asymmetry 14 (2003) 3639
48. Gou D.-M., Liu Y.-C., and Chen C.-S. J. Org. Chem. 58 (1993) 1287
49. An analogous stereochemical interconversion of 1,3-aminoalcohols via the formation of intermediate oxazines, see:. Singh O.V., Kampf D.J., and Han H. Tetrahedron Lett. 45 (2004) 7239