Stereocontrolled synthesis of 2-amino-2-deoxy-α-D-C-glycopyranosides by radical cyclization reactions

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9193-9194

  Czernecki, Stanislas ^a   Ayadi, Ebtissam ^a   Xie, Juan ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Amino D C glycoside; Radical cyclisation

Indexed keywords

GLYCOPYRANOSIDE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030590967     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02153-3     Document Type: Article

References (18)

1. 1. Curran, D. P. Synthesis 1988, 417-439.
2. 2. (a) Barlett, P. A.; Mclaren, K. L.; Ting, P. C. J. Am. Chem. Soc. 1988, 10, 1633-1634.
3. (b) Velazquez, S.; Jimeno, M. L.; Huss, S.; Balzarini, J.; Camarasa, M. J. J. Org. Chem. 1994, 59, 7661-7670.
4. 3. (a) Giese B. Angew. Chem., Int. Ed. Engl. 1985, 24, 553-565.
5. (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073-3100.
6. (c) Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
7. (d) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959-974.
8. (e) Xi, Z.; Glemarec, C.; Chattopadhyaya, J. Tetrahedron 1993, 49, 7525-7546.
9. 4. Postema, M. H. D. Tetrahedron 1992, 48, 8545-8599.
10. 5. (a) De Mesmaeker, A.; Waldner, N.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1990, 687-690.
11. (b) De Mesmaeker, A.; Waldner, N.; Hoffmann, P.; Mindt, T.; Hug, P.; Winkler, T. Synlett 1992, 285-290.
12. 6. Abel, S.; Linker, T.; Giese, B. Synlett 1991, 171-172.
13. 7. Czernecki, S.; Ayadi, E.; Randriamandinby, D. J. Org. Chem. 1994, 59, 8256-8260.
14. 13C-NMR) in agreement with their structure.
15. 9. (a) Guindon, Y.; Lavallée, J. F.; Boisvert, L.; Chabot, C.; Delorme, D.; Yoakim, C.; Hall, D.; Lemieux, R. V.; Simoneau, B. Tetrahedron Lett. 1991, 32, 27-30.
16. (b) Becouarn, S.; Czernecki, S.; Valéry, J. M. Tetrahedron Lett. 1995, 36, 873-876.
17. 10. (a) Korth, H. G.; Sustmann, R.; Dupuis, J.; Giese, B. J. Chem. Soc., Perkin Trans. 11 1986, 1453-1459.
18. (b) Korth, H. G.; Sustmann, R.; Giese, B.; Rückert, B.; Gröninger, K. S. Chem. Ber. 1990, 123, 1891-1898.