Stereoselective synthesis of differentially protected derivatives of the higher amino sugars destomic acid and lincosamine from serine and threonine

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 581-586

  Marshall, James A ^a   Beaudoin, Serge ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; AMINOSUGAR; DESTOMIC ACID; LINCOSAMINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030059843     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9517914     Document Type: Article

References (40)

1. (a) Marshall, J. A ; Beaudoin, S. J. Org. Chem. 1994, 59, 6614.
2. (b) Marshall, J. A.; Beaudoin, S. J. Org. Chem. 1994, 59, 7833.
3. Fischer, E. Liebigs Ann. Chem. 1895, 288, 150.
4. Ikemoto, N.; Schreiber, S. J. Am. Chem. Soc. 1992, 114, 2524.
5. Cf. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4794.
6. Cf. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4794.
7. Cf. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531. Dondoni, A.; Perrone, D. J. Org. Chem. 1995, 60, 4794.
8. (a) For a previous synthesis from D-galactose, see Hashimoto, H.; Asano, K.; Fujii, F.; Yoshimura, J. Carbohydr. Res. 1982, 104, 87.
9. (b) For a recent approach see Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344.
10. (c) Dondoni, A.; Franco, S.; Merchan, F.; Merino, P.; Tejero, T. Synlett 1993, 78.
11. (a) Garner, P.; Park, J.-M. J. Org. Chem. 1987, 52, 2361.
12. (b) Garner, P.; Park, J.-M. Org. Synth. 1991, 70, 18.
13. (c) McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31.
14. Cf. (a) Saito, S.; Narahara, O.; Ishikawa, T.; Asahara, M.; Moriwake, T.; Gawronski, J.; Kazimiercyzk, F. J. Org. Chem. 1993, 58, 6292. (b) Gung, B. W.; Melnick, J. P.; Wolf, M. A.; Marshall, J. A. Beaudoin, S. J. Org. Chem. 1994, 59, 5609.
15. Cf. (a) Saito, S.; Narahara, O.; Ishikawa, T.; Asahara, M.; Moriwake, T.; Gawronski, J.; Kazimiercyzk, F. J. Org. Chem. 1993, 58, 6292. (b) Gung, B. W.; Melnick, J. P.; Wolf, M. A.; Marshall, J. A. Beaudoin, S. J. Org. Chem. 1994, 59, 5609.
16. VanRheenen, V.; Kelly, R. C.; Chas, D. Y. Tetrahedron Lett. 1976, 1973.
17. Cf (a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947. (b) Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 24, 3951.
18. Cf (a) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947. (b) Stork, G.; Kahn, M. Tetrahedron Lett. 1983, 24, 3951.
19. (a) Cf. Krysan, D. J.; Rockway, T. W.; Haight, A. R. Tetrahedron Asymmetry 1994, 5, 625 and references therein.
20. (b) For a recent review, see Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761.
21. Slomp, G.; MacKellar, F. A. J. Am. Chem. Soc. 1967, 89, 2454.
22. (a) Magerlein, B. J. Tetrahedron Lett. 1970, 33.
23. (b) Howarth, G. B.; Szarek, W. A.; Jones, J. K. N. J. Chem. Soc. (C) 1970, 2218.
24. (c) Saeki, S.; Ohki, E. Chem. Pharm. Bull. 1970, 18, 789.
25. (d) Fukumaru, T.; Atsumi, T.; Ogawa, T.; Matsui, M. Agr. Biol. Chem. 1973, 37, 2617.
26. (e) Woolard, G. R.; Rathbone, E. B.; Szarek, W. A.; Jones, J. K. N. J. Chem. Soc. Perkin Trans. 1 1976, 950.
27. (f) Gateau-Olesker, A.; Sepulchre, A. M.; Vass, G.; Gíro, S. D. Tetrahedron 1977, 33, 393.
28. (g) Hoppe, I.; Schöllkopf, U. Liebigs Ann. Chem. 1980, 1474.
29. (h) Knapp, S.; Kukkola, P. J. J. Org. Chem. 1990, 55 1632.
30. (a) Larson, E. R.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 6715.
31. (b) Danishefsky, S.; Larson, E.; Springer, J. P. J. Am. Chem. Soc. 1985, 107, 1274.
32. (c) Danishefsky, S.; DeNinno, M. P.; Schulte, G. J. Org. Chem. 1987, 52, 3173.
33. (d) Golebiowski, A.; Jurczak, J.; Krajewski, J. W.; Galilskii, N. M ; Vernich, A J. Bull. Polish Acad. Sci. 1989, 37, 307.
34. (e) Golebiowski, A.; Jurczak, J. Tetrahedron 1991, 47, 1045.
35. (f) Szechner, B.; Achmatowicz, O. J. Carbohydrate Chem 1992, 11, 401.
36. Wadsworth, W. S., Jr. Org. React. 1977, 25, 73.
37. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3107. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
38. Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3107. Dodge, J. A.; Trujillo, J. I.; Presnell, M. J. Org. Chem. 1994, 59, 234.
39. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
40. -1. For a summary of experimental protocols, see Marshall, J. A.; Wang, X.-J. J. Org. Chem. 1991, 56, 960.