Aryl and Allyl C-Glycosidation Methods Using Unprotected Sugars

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2307-2313

  Toshima, Kazunobu ^a   Matsuo, Goh ^a   Ishizuka, Toru ^a   Ushiki, Yasunobu ^a   Nakata, Masaya ^a   Matsumura, Shuichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001111947     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972146v     Document Type: Article

References (34)

1. Taken in part from the Ph.D. Thesis of Goh Matsuo, Keio University, 1997.
2. For recent reviews of C-glycosidation method, see: (a) Postema, M. H. D. Tetrahedron 1992, 40, 8545. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995.
3. For recent reviews of C-glycosidation method, see: (a) Postema, M. H. D. Tetrahedron 1992, 40, 8545. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995.
4. For a recent review of O-glycosidation method, see: Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
5. For our preliminary communications on aryl C-glycosidation, see: (a) Toshima, K.; Matsuo, G.; Tatsuta, K. Tetrahedron Lett. 1992, 33, 2175. (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Nakata, M.; Kinoshita, M. J. Chem. Soc., Chem. Commun. 1992, 1641. (c) Toshima, K.; Matsuo, G.; Nakata, M. J. Chem. Soc., Chem. Commun. 1994, 997.
6. For our preliminary communications on aryl C-glycosidation, see: (a) Toshima, K.; Matsuo, G.; Tatsuta, K. Tetrahedron Lett. 1992, 33, 2175. (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Nakata, M.; Kinoshita, M. J. Chem. Soc., Chem. Commun. 1992, 1641. (c) Toshima, K.; Matsuo, G.; Nakata, M. J. Chem. Soc., Chem. Commun. 1994, 997.
7. For our preliminary communications on aryl C-glycosidation, see: (a) Toshima, K.; Matsuo, G.; Tatsuta, K. Tetrahedron Lett. 1992, 33, 2175. (b) Toshima, K.; Matsuo, G.; Ishizuka, T.; Nakata, M.; Kinoshita, M. J. Chem. Soc., Chem. Commun. 1992, 1641. (c) Toshima, K.; Matsuo, G.; Nakata, M. J. Chem. Soc., Chem. Commun. 1994, 997.
8. For our preliminary communication on allyl C-glycosidation, see: Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M. Tetrahedron Lett. 1994, 35, 5673.
9. For a recent review of angucycline antibiotics, see: Rohr, J.; Thiericke, R. Nat. Prod. Rep. 1992, 103.
10. For a recent review of pluramycin antibiotics, see: Hansen, M. R.; Hurley, L. H. Acc. Chem. Res. 1996, 29, 249.
11. Kometani, T.; Kondo, H.; Fujimori, Y. Synthesis 1988, 1005.
12. (a) Matsumoto, T.; Katsuki, M.; Suzuki, K. Tetrahedron Lett. 1988, 29, 6935.
13. (b) Matsumoto, T.; Katsuki, T.; Jona, H.; Suzuki, K. J. Am. Chem. Soc. 1991, 113, 6982.
14. 1H NOE experiments of the aromatic moiety.
15. For other representative aryl C-glycosidations via O→C-glycoside migration, see: (a) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett. 1992, 33, 3061. (b) Gasiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett. 1988, 29, 3323. (c) Mahling, J.-A.; Schmidt, R. R. Synthesis 1993, 325.
16. For other representative aryl C-glycosidations via O→C-glycoside migration, see: (a) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett. 1992, 33, 3061. (b) Gasiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett. 1988, 29, 3323. (c) Mahling, J.-A.; Schmidt, R. R. Synthesis 1993, 325.
17. For other representative aryl C-glycosidations via O→C-glycoside migration, see: (a) Ramesh, N. G.; Balasubramanian, K. K. Tetrahedron Lett. 1992, 33, 3061. (b) Gasiraghi, G.; Cornia, M.; Rassu, G.; Zetta, L.; Fava, G. G.; Belicchi, M. F. Tetrahedron Lett. 1988, 29, 3323. (c) Mahling, J.-A.; Schmidt, R. R. Synthesis 1993, 325.
18. Barton, T. J.; Tully, C. R. J. Org. Chem. 1978, 43, 3649.
19. Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864.
20. For representative application to natural products syntheses, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. J. Chem. Soc., Chem. Commun. 1985, 1359. (b) Wincott, F. E.; Danishefsky, S. J.; Schulte, G. Tetrahedron Lett. 1987, 28, 4951. (c) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. (d) Ichikawa, Y.; Isobe, M.; Goto, T. Tetrahedron 1987, 43, 4749.
21. For representative application to natural products syntheses, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. J. Chem. Soc., Chem. Commun. 1985, 1359. (b) Wincott, F. E.; Danishefsky, S. J.; Schulte, G. Tetrahedron Lett. 1987, 28, 4951. (c) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. (d) Ichikawa, Y.; Isobe, M.; Goto, T. Tetrahedron 1987, 43, 4749.
22. For representative application to natural products syntheses, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. J. Chem. Soc., Chem. Commun. 1985, 1359. (b) Wincott, F. E.; Danishefsky, S. J.; Schulte, G. Tetrahedron Lett. 1987, 28, 4951. (c) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. (d) Ichikawa, Y.; Isobe, M.; Goto, T. Tetrahedron 1987, 43, 4749.
23. For representative application to natural products syntheses, see: (a) Nicolaou, K. C.; Duggan, M. E.; Hwang, C.-K.; Somers, P. K. J. Chem. Soc., Chem. Commun. 1985, 1359. (b) Wincott, F. E.; Danishefsky, S. J.; Schulte, G. Tetrahedron Lett. 1987, 28, 4951. (c) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082. (d) Ichikawa, Y.; Isobe, M.; Goto, T. Tetrahedron 1987, 43, 4749.
24. (a) Ferrier, R. J. Chem. Soc. 1964, 5443.
25. (b) Ferrier, R.; Prasad, N. J. Chem. Soc. C 1969, 570.
26. (a) Danishefsky, S.; Kerwin, J. F. Jr. J. Org. Chem. 1982, 47, 3803.
27. (b) Ichikawa, Y.; Isobe, M.; Konobe, M.; Goto, T. Carbohydr. Res. 1887, 171, 193.
28. (c) Toshima, K.; Ishizuka, T.; Matsuo, G.; Nakata, M. Chem. Lett. 1993, 2013.
29. Toshima, K.; Miyamoto, N.; Matsuo, G.; Nakata, M.; Matsumura, S. Chem. Commun. 1996, 1379.
30. The α-configurations of the anomeric positions were confirmed by the comparison between the corresponding acetylated glycosides, which were obtained by standard acetylation, and the authentic samples reported in ref 16.
31. (a) Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976.
32. (b) Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370.
33. For our preliminary communications of those works, see: (a) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225. (b) Matsuo, G.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 2173.
34. For our preliminary communications of those works, see: (a) Matsuo, G.; Miki, Y.; Nakata, M.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 225. (b) Matsuo, G.; Matsumura, S.; Toshima, K. Chem. Commun. 1996, 2173.