A facile transformation of the δ-hydroxy-α-amino lactones from α- furfuryl amide

Tetrahedron

Volumn 54, Issue 41, 1998, Pages 12571-12584

  Liao, Li Xin ^a   Zhou, Wei Shan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; LACTONE DERIVATIVE; OZONE;

ARTICLE; CONFORMATIONAL TRANSITION; EPOXIDATION; HYDROGENATION; HYDROXYLATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032497685     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00736-4     Document Type: Article

References (30)

1. 1. Greenstein, J. P. and Wintiz, M. "Chemistry of Amino acids" New York, London, 1961, Vol. 1, P. 3.
2. 2. a) Weinstein, B. "Chemistry and Biochemistry of Amino Acids, Peptides, and Proteins", 1971, Vol. 4, P. 2.
3. b) Barett, G. C. "Chemistry and Biochemistry of Amino Acids", (ed) Chapmann and Hall, London, New York, 1985.
4. 3. Miller, M. J., Acc. Chem. Res., 1986, 19, 49, and references therein.
5. 4. a) Higgens, C. E. and Kastner, R. E., Int. J. Syst. Bacteriol., 1971, 21, 326;
6. b) Evans, R. H., H.AX, Jr., Jacoby, A., Williams, T. H., Jenkins, E. and Scannell, J. P., J. Antibiotics, 1983, 36, 208;
7. c) Preuss, D. L. and Kellet, M., J. Antibiotics, 1983, 36, 213;
8. d) Muller, J-C., Toome, V., Preuss, D. L., Blount, J. F. and Weigele, M., J. Antibiotics, 1983, 36, 217.
9. 5. Bernardo, S. D., Tengi, J. P., Sasso, G. J. and Weigele, M., J. Org. Chem., 1985, 50, 3457.
10. 6. Williams, R. M., Sinclair, P. J., Zhai, D. and Chen, D., J. Am. Chem. Soc., 1988, 110, 1547.
11. 7. a) Ariza, J., Font, J. and Ortuno, R. M., Tetrahedron Lett., 1991, 32, 1979;
12. b) Ariza, J., Diaz, M., Font, J. and Ortuno, R. M., Tetrahedron, 1993, 49, 1315.
13. 8. Schmidt, U. Lieberknecht, A., Kazmaier, U., Gunther, J. and Metzger, J., Synthesis, 1991, 49.
14. 9. Preliminary communication see: Liao, L. X. and Zhou, W. S., Tetrahedron Lett., 1996, 37, 6371.
15. 10 a) Zhou, W. S., Lu, Z. H. and Wang, Z. M., Tetrahedron Lett., 1991, 32, 1467;
16. b) Zhou, W. S., Lu, Z. H. and Wang, Z. M., Tetrahedron, 1993, 49, 2641.
17. 11. a) Sharpless, K. B., Amberg, W., Bennani, Y. L., Crispino, G. A., Hartung, J., Jeong, K-S., Kwong, H.-L., Morikawa, K., Wang, Z. M., Xu, D., Zhang, X.-L., J. Org. Chem., 1992, 57, 2768;
18. b) Crispino, G. A., Jeong, K-S., Koib, H. C., Wang, Z. M., Zhang, X.-L., J. Org. Chem., 1993, 58, 4585.
19. 12. a) Lu, Z. H. and Zhou, W. S., J. Chem. Soc., Perkin Trans I,1993, 593;
20. b) Zhou, W. S., Xie, W. G., Lu, Z. H. and Pan, X. F., Tetrahedron Lett., 1995, 36, 1291;
21. c) Zhou, W. S., Xie, W. G., Lu, Z. H. and Pan, X. F., J. Chem. Soc. Perkin Trans I, 1995, 2599;
22. d) Lu, Z. H. and Zhou, W. S., Tetrahedron, 1993, 49, 4659;
23. e) Xu, Y. M. and Zhou, W. S., Tetrahedron Lett., 1996, 37, 1461;
24. f) Xu, Y. M. and Zhou, W. S., J. Chem. Soc. Perkin Trans I, 1997, 741.
25. 13. Zhou, W. S., Lu, Z. H. and Zhu, X. Y., Chinese J. Chem., 1994, 12, 378.
26. 14. Carlsen, P. H., Katsuki, T., Martin, V. S. and Sharpless, K. B., J. Org. Chem., 1981, 46, 3936.
27. 15. Killers, S., Niklaus, A. and Reiser, O., J. Org. Chem., 1993, 58, 3169.
28. 16. Liao, L.X., Wang, Z. M., Zhou, W. S., Tetrahedron: Asymmetry, 1997, 12, 1951.
29. 17. Elamin, B., Anantharamaiah, G. M., Royer, G. P., Means, G. E., J. Org. Chem., 1979, 44, 3442.
30. 18. Martin, V. S.; Woodard, S. S.; Katastuki, T.; Yamada, M.; Sharpless, K. B., J. Am. Chem. Soc., 1981, 103, 6237.