Highly β-selective C-allylation of a ribofuranoside controlling steric hindrance in the transition state

Organic Letters

Volumn 10, Issue 22, 2008, Pages 5107-5110

  Ichikawa, Satoshi ^a   Hayashi, Ryoko ^a   Hirano, Shinpei ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,3 O (3 PENTYLIDENE) D RIBOFURANOSYL FLUORIDE; 2,3-O-(3-PENTYLIDENE)-D-RIBOFURANOSYL FLUORIDE; ALKENE; FLUORIDE; MONOSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; ENZYME SPECIFICITY; STEREOISOMERISM;

ALKENES; FLUORIDES; MONOSACCHARIDES; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 58149195372     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8018743     Document Type: Article

References (41)

1. Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Tarrytown, NY, 1995; Vol. 13.
2. Postema, M. H. D. C-Glycoside Synthesis; CRC Press: Boca Raton, FL, 1995.
3. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913-9959.
4. Wu, Q.; Simons, C. Synthesis 2004, 1533-1553.
5. Harmange, J.-C.; Figadere, B. Tetrahedron: Asymmetry 1993, 4, 1711-1754.
6. N2-type mechanism: Callam, C. S.; Gadikota, R. R.; Krein, D. M.; Lowary, T. L. J. Am. Chem. Soc. 2003, 125, 13112-13119.
7. (a) Stevens, R. V.; Lee, A. W. M. J. Am. Chem. Soc. 1979, 101, 7032-7035.
8. (b) Stevens, R. V. Acc. Chem. Res. 1984, 17, 289-296.
9. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon: New York, 1983; pp 209-221.
10. (a) Araki, Y.; Kobayashi, N.; Ishido, Y.; Nagasawa, J. Carbohydr. Res. 1987, 171, 125-139.
11. (b) Mukaiyama, T.; Kobayashi, S. Carbohydr. Res. 1987, 171, 81-87.
12. (c) Mukaiyama, T.; Kobayashi, S.; Shoda, S. Chem. Lett. 1984, 1529-1530.
13. (d) Tomooka, K.; Matsuzawa, K.; Suzuki, K.; Tsuchihashi, G. Tetrahedron Lett. 1987, 28, 6339-6342.
14. Jaouen, V.; Jegou, A.; Lemee, L.; Veyrieres, A. Tetrahedron 1999, 55, 9245-9262.
15. Nishiyama, Y.; Katoh, T.; Deguchi, K.; Morimoto, Y.; Itoh, K. J. Org. Chem. 1997, 62, 9339-9341.
16. (a) Schmitt, A.; Reissig, H.-U. Synlett 1990, 10, 1-94.
17. (b) Schmitt, A.; Reissig, H.-U. Chem. Ber. 1995, 128, 871-876.
18. (c) Schmitt, A.; Reissig, H.-U. Eur. J. Org. Chem. 2000, 3893-3901.
19. (d) Schmitt, A.; Reissig, H.-U. Eur. J. Org. Chem. 2001, 116, 9-1174.
20. (a) Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 6706-6707.
21. (b) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208-12209.
22. (c) Smith, D. M.; Tran, M. B.; Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 14149-14152.
23. (d) Smith, D. M.; Woerpel, K. A. Org. Lett. 2004, 6, 2063-2066.
24. (e) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Smith, D. M.; Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 10879-10884.
25. Jung, K.; Muller, M.; Schmidt, R. Chem. Rev. 2000, 100, 4423-4442.
26. Kozikowski, A. P.; Sorgi, K. L. Tetrahedronn Lett. 1983, 24, 1563-1566.
27. McDevitt, J. P.; Lansbury, P. T. J. Am. Chem. Soc. 1996, 118, 3818-3828.
28. Alternatively, β-C-furanosides can be stereoselectively prepared by a two-step sequence involving nucleophilic addition of a suitably protected ribonic γ-lactone followed by Lewis acid-promoted silane reduction. For examples, see: (a) Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. J. Org. Chem. 1997, 62, 3453-3459.
29. (b) Calzada, E.; Clarke, C. A.; Roussin-Bouchard, C.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1995, 517-518.
30. Keck, G. E.; Enholm, E. J.; Kachensky, D. F. Tetrahedron Lett. 1984, 25, 1867-1870.
31. Saito, T.; Nishimoto, Y.; Yasuda, M.; Baba, A. J. Org. Chem. 2006, 71, 8516-8522.
32. Hirano, S.; Ichikawa, S.; Matsuda, A. Angew. Chem., Int. Ed. 2005, 44, 1854-1856.
33. Hirano, S.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2007, 72, 9936-9946.
34. Hirano, S.; Ichikawa, S.; Matsuda, A. Tetrahedron 2007, 63, 2798-2804.
35. Hirano, S.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2008, 73, 569-577.
36. β-Fluoride was used in this study to clarify the reaction conditions. The reaction with the corresponding α-fluoride gave the similar results although not optimized.
37. Wilcox, C. S.; Otoski, R. M. Tetrahedron Lett. 1986, 27, 1011-1014.
38. Hosomi, A.; Hashimoto, H.; Sakurai, H. Tetrahedron Lett. 1980, 21, 951-954.
39. This was prepared by a cross-metathesis reaction of methyl acrylate and allyltrimethylsilane in a manner similar to the procedure previouly reported.
40. Evans, D. A.; Aye, Y.; Wu, J. Org. Lett. 2006, 8, 2071-2073.
41. Blanco, O. M.; Castedo, L. Synlett 1999, 5, 557-558.