Efficient synthesis of β-C-glucosides via radical cyclization with a silicon tether based on the conformational restriction strategy

Tetrahedron Letters

Volumn 46, Issue 38, 2005, Pages 6555-6558

  Terauchi, Masaru ^a   Matsuda, Akira ^a   Shuto, Satoshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSIDE; SILICON;

ARTICLE; CONFORMATION; CYCLIZATION; SYNTHESIS;

EID: 23844502411     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.07.087     Document Type: Article

References (28)

1. M.H.D. Postema Tetrahedron 48 1992 8545 8599
2. C. Jaramillo, and S. Knapp Synthesis 1994 1 20
3. D.E. Levy, and C. Tang The Chemistry of C-Glycosides 1995 Pergamon Press Oxford
4. M.H.D. Postema C-Glycoside Synthesis 1995 CRC Press Boca Raton
5. S. Shuto, K. Tatani, Y. Ueno, and A. Matsuda J. Org. Chem. 63 1998 8815 8824
6. H. Abe, S. Shuto, and A. Matsuda J. Org. Chem. 65 2000 4315 4325
7. S. Shuto, Y. Yahiro, S. Ichikawa, and A. Matsuda J. Org. Chem. 65 2000 5547 5557
8. M. Terauchi, Y. Yahiro, H. Abe, S. Ichikawa, S.C. Tovey, S.G. Dedos, C.W. Taylor, V.B.L. Potter, A. Matsuda, and S. Shuto Tetrahedron 61 2005 3697 3707
9. S. Ichikawa, S. Shuto, and A. Matsuda Tetrahedron Lett. 39 1998 4525 4528
10. Y. Yahiro, S. Ichikawa, S. Shuto, and A. Matsuda Tetrahedron Lett. 40 1999 5527 5531
11. H. Abe, S. Shuto, and A. Matsuda J. Am. Chem. Soc. 123 2001 11870 11882
12. S. Tamura, H. Abe, A. Matsuda, and S. Shuto Angew. Chem., Int. Ed. 42 2003 1021 1023 and references cited therein
13. G. Stork, H.S. Suh, and G. Kim J. Am. Chem. Soc. 113 1991 7054 7055
14. Radical reactions with a vinylsilyl group as a tether: S. Shuto, M. Kanazaki, S. Ichikawa, and A. Matsuda J. Org. Chem. 62 1997 5676 5677
15. I. Sugimoto, S. Shuto, and A. Matsuda J. Org. Chem. 64 1999 7153 7157
16. S. Shuto, I. Sugimoto, and A. Matsuda J. Am. Chem. Soc. 122 2000 1343 1351 and references cited therein
17. Radical reactions with an allylsilyl group as a tether: Z. Xi, P. Agback, J. Plavec, A. Sandström, and J. Chattopadhyaya Tetrahedron 48 1992 349 370
18. M. Kanazaki, Y. Ueno, S. Shuto, and A. Matsuda J. Am. Chem. Soc. 122 2000 2422 2432
19. Conformational restriction of pyranoses by bulky silyl-protecting groups: A.M. Tius, and J. Bushe-Petersen Tetrahedron Lett. 29 1994 5181 5184
20. T. Hosoya, Y. Ohashi, T. Matsumoto, and K. Suzuki Tetrahedron Lett. 37 1996 663 666
21. C. Walford, R.F.W. Jackson, N.H. Rees, W. Clegg, and S.L. Heath Chem. Commun. 1997 1855 1856
22. T. Ikeda, and H. Yamada Carbohydr. Res. 329 2000 889 893
23. H. Abe, M. Terauchi, A. Matsuda, and S. Shuto J. Org. Chem. 68 2003 7439 7447 and references cited therein
24. 4,5 = 8.7 Hz.
25. The anomeric β-stereochemistry of the cyclization products 10 and 11 was confirmed by NOE experiments.
26. The eight- and nine-membered ring formations in radical reactions are known to occur usually via endo-mode cyclization: A. Srikrishna P. Renaud M.P. Sibi Radicals in Organic Synthesis Vol. 2 2001 Wiley-VCH Weinheim 151 187
27. I. Fleming, R. Henning, and H. Plaut J. Chem. Soc., Chem. Commun. 1984 29 31
28. 4-conformational restriction strategy is also effective in the radical cyclization to synthesize α-C-glycosides: Ref. 2c,d.