RCM approaches toward the diastereoselective synthesis of vicinal trans-diaminocyclitols from L-serine

Journal of Organic Chemistry

Volumn 69, Issue 16, 2004, Pages 5314-5321

  Cong, Xin ^a,b   Liao, Qing Jiang ^b   Yao, Zhu Jun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; DERIVATIVES; ENZYME INHIBITION; ENZYMES; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLEFINS; OXIDATION; STEREOCHEMISTRY; SUGAR (SUCROSE); SYNTHESIS (CHEMICAL);

EPOXIDATION; POLYHYDROXYLIC GROUPS;

ALCOHOLS;

ACRYLIC ACID; ALKENE; GLYCOSIDASE INHIBITOR; SERINE;

ARTICLE; DIASTEREOISOMER; DIHYDROXYLATION; EPOXIDATION; GRIGNARD REACTION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

CATALYSIS; ENZYME INHIBITORS; GLYCOSIDE HYDROLASES; HEXOSAMINES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SERINE; STEREOISOMERISM;

EID: 3543032189     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0496547     Document Type: Article

References (30)

1. (a) Lillelund, V. H.; Jensen, H. H.; Liang, X.; Bols, M. Chem. Rev. 2002, 102, 515-553.
2. (b) Butters, T. D.; Dwek, R. A.; Platt, F. M. Chem. Rev. 2000, 100, 4683-4696.
3. Wang, L. X.; Sakairi, N.; Kuzuhara, H. Carbohydr. Res. 1995, 275, 33-47.
4. (a) Takahata, H.; Banba, Y.; Ouchi, H.; Nemoto, H. Org. Lett. 2003, 5, 2527-2529.
5. (b) Subramanian, T.; Lin, C. C.; Lin, C. C. Tetrahedron Lett. 2001, 42, 4079-4082.
6. (c) Heck, M. P.; Vincent, S. P.; Murray, B. W.; Bellamy, F.; Wong, C. H.; Mioskowski, C. J. Am. Chem. Soc. 2004, 126, 1971-1979.
7. Kwon, Y. U.; Lee, C.; Chung, S. K. J. Org. Chem. 2002, 67, 3327-3338.
8. (a) Paul, B. J.; Hobbs, E.; Buccino, P.; Hudlicky, T. Tetrahedron Lett. 2001, 42, 6433-6435.
9. (b) Russell, R. J. M.; Murray, J. B.; Lentzen, G.; Haddad, J.; Mobashery, S. J. Am. Chem. Soc. 2004, 126, 3410-3411.
10. Takahata, H.; Banba, Y.; Ouchi, H.; Nemoto, H.; Kato, A.; Adachi, I. J. Org. Chem. 2003, 68, 3603-3607.
11. (a) Schurrle, K.; Beier, B.; Piepersberg, W. J. Chem. Soc., Perkin Trans. 1991, 1, 2407-2412.
12. (b) Sakairi, N.; Hayashida, M.; Amano, A.; Kuzuhara, H. J. Chem. Soc., Perkin Trans. 1990, 1, 1301-1313.
13. (a) Guedat, P.; Spieb, B.; Schlewer, G. Tetrahedron Lett. 1994, 35, 7375-7378.
14. (b) Kresze, G.; Weiss, M. M.; Dittel, W. Liebigs Ann. Chem. 1984, 203-212.
15. (a) Wang, J.; Vina, D.; Busson, R.; Herdewijn, P. J. Org. Chem. 2003, 68, 4499-4505.
16. (b) Kim, K. H.; Miller, M. J. Tetrahedron Lett. 2003, 44, 4571-4573.
17. (a) Badorrey, R.; Cativiela, C.; Diaz-de-Villegas, M. D.; Diez, R.; Galvez, J. A. Tetrahedron Lett. 2004, 45, 719-722.
18. (b) Soengas, R. G.; Estevez, J. C.; Estevez, R. J. Org. Lett. 2003, 5, 1423-1425.
19. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
20. Toda, A.; Mimura, A. N.; Ohno, H.; Fujii, N.; Ibuka, T. J. Org. Chem. 1998, 63, 7053-7061.
21. Merino, P.; Anoro, S.; Franco, S.; Gascon, J. M.; Martin, V.; Merchan, F. L.; Revuelta, J.; Tejero, T.; Tunon, V. Synth. Commun. 2000, 30, 2989-3021.
22. (a) Mckillop, A.; Taylor, R. J. K.; Waston, R. J.; Lewis, N. Synthesis 1994, 3, 31-33.
23. (b) Dondoni, A.; Perrone, P. Synthesis 1997, 5, 527-529.
24. (c) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364.
25. (a) Merino, P.; Lanaspa, A.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1998, 9, 629-646.
26. (b) Merino, P.; Castillo, E.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron 1998, 54, 12301-12322.
27. Crotti, P.; Bussolo, V. D.; Favero, L.; Pineschi, M.; Marianucci, F.; Renzi, G.; Amici, G.; Roselli, G. Tetrahedron 2000, 56, 7513-7524.
28. Baron, E.; O'Brien, P.; Towers, T. D. Tetrahedron Lett. 2002, 43, 723-726.
29. Crimmins, M. T.; Tabet. E. A. J. Org. Chem. 2001, 66, 4012-4018.
30. Borch, R. F.; Bernstein, M. D.; Durst, H. D. J. Am. Chem. Soc. 1971, 93, 2897-2904.