Abstract
These types of glycosides have attracted much attention, considering that many of them have demonstrated their effectiveness as therapeutic agents. The increasing significance of C-glycosides is that the conformational differences compared to O- or N-glycosides are minimal and that they are resistant to enzymatic or acidic hydrolysis since the anomeric center has been transformed from acetal to ether. A glycoside is defined as C-glycoside when what it is suppose to be the anomeric carbon of a sugar is interconnected to the aglycon, generating a new C-C bond. According to Levy and Tang the term C-glycoside describes those structures in which a common structural motifs the presence of carbon functionality at what would otherwise be the anomeric position of a sugar or derivative. Structurally C-glycosides can be constituted by aliphatic, or aromatic aglycon, and the sugar can be pyranose or furanose. A variety of natural product C-glycosides has been described. Examples of C-glycosides isolated from different plant genus and characterized spectroscopically are: Carminic acid, Aloin, Scoparin, Saponarin, and more recently Cucumerins (flavonoid phytoalexins) and C-glucosylxanthones and complex benzoquinone Altromycin B among others (Figure 5.1).
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References
P.S. Belica, and R.W. Franck, Tetrahedron Lett. 39, 8225 (1998).
D.E. Levy, and C. Tang, The Chemistry of C-Glycosides, Pergamon Press: Oxford (1995).
D.J. McNally, K.V. Wurms, C. Labbé, S. Quideau, and R.R. Belanger, J. Nat. Prod. 66, 1280 (2003).
P.M. Pauletti, I. Castro-Gamboa, D.H. Siqueira-Silva, M.C. Marx-Young, D.M. Tomazela, M.N. Eberlin, V. da Silva-Bolzani, J. Nat. Prod. 66, 1384 (2003).
P. Pasetto and W. Franck, J. Org. Chem. 68, 8042 (2003).
R.E. Dolle and K.C. Niclolaou, J. Am. Chem. Soc. 107, 1691 (1985).
R.E. Ireland, R.C. Anderson, R. Badoub, B. Fitzsimmons, S. McGarvey, S. Thaissivongs, and C.S. Wicox, J. Am. Chem. Soc., 105, 1983 (1983).
F. Emery and P. Vogel, Tetrahedron Lett. 4209 (1993).
L. Paterson and L.E. Keown, Tetrahedron Lett. 38, 5727 (1997).
M.D. Lewis, J.K. Cha, and Y. Kishi, J. Am. Chem. Soc. 104, 4976 (1982).
Y. Du, R.J. Linhardt, and I. Vlahov, Tetrahedron 54, 9913 (1998).
(a) M.H.D. Postema, C-glycoside Synthesis; CRC Press: Boca Ratón (1995); b) M.H.D. Postema Tetrahedron 48, 8545 (1992).
P. Sinaÿ, Pure & Appl. Chem. 69, 459 (1997).
J. Gervay, and M.J. Hadd, J. Org. Chem. 62, 6961 (1997).
K. Oyama and T.J. Kondo, Org. Chem. 69, 5240 (2004).
E. Calzada, C.A. Clarke, C. Roussin-Bouchard, and R.H. Wightman, J. Chem. Soc. Perkin Trans 1, 717 (1995).
R.W. Schmidt, B. Frick, B. Haag-Zeino and S. Apparao, Tetrahedron Lett. 28, 4045 (1987).
J.M. Lancelin, J.R. Pougny, and P. Sinaÿ, Carbohydr. Res. 136, 369 (1985).
D. Craig, M.W. Pennington, and P. Warner, Tetrahedron 55, 13495 (1999).
R.R. Schmidt and P. Shorma, Carbohydr. Res. 14, 1353 (1985).
M.A. Tius, J. Gomez-Galano, X. Gu, and J.H. Zaidi, J. Am. Chem. Soc. 113, 5775 (1991).
A. Abas, R.L. Beddoes, J.C. Conway, P. Quayle, and C.J. Urch, Synlett, 1264 (1995).
B.A. Johns, Y.T. Pan, A.D. Elbein, and C.R. Johnson, Carbohydr. Res. 136, 369 (1985).
T. Kometani, H. Kondo, and Y. Fujimori, Synthesis 1005 (1988).
F. Burkhart, M. Hoffmann, and H. Kessler, Angew. Chem. Int. Ed. Engl. 36, 1191 (1997).
K.A. Parker and C.A. Coburn, J. Am. Chem. Soc. 113, 8516 (1991).
O.R. Martin and W. Lai, J. Org. Chem. 58, 176 (1993).
(a) P. Schawab, M.B. France, J.W. Ziller, and R.H. Grubbs, Angew. Chem., Int, Ed. Engl. 34, 2039 (1995). (b) M.H.D Postema, J.L. Piper, and R.L. Betts, J. Org. Chem. 70, 829 (2005).
R. Roy, R. Dominique, and S.K. Das, J. Org. Chem. 64, 5408 (1999).
T. Mazéas, J.M. Skrydstrup, and J.M. Beau, Angew. Chem, 107, 990 (1995).
S.L. Krintel, J. Jiménez-Barbero, and T. Skrydstrup, Tetrahedron Lett., 40, 7565 (1999).
A. Dondoni and A. Marra, Chem. Rev. 100, 4395 (2000).
Y. Ohnishi and Y. Ichikawa, Bioorg. Med. Chem. Lett. 12, 997 (2002).
G. Yang, R.W. Franck, R. Bittman, P. Samadder, and G. Arthur, Org. Lett. 3, 197 (2001).
F.K. Griffin, D.E. Paterson, and R.J. Taylor, Angew. Chem., Int. Ed. 38, 2939 (1999).
H. Togo, W. He, and Y. Waki, and M. Yokohama, Synlett 700 (1998).
A. Chenede, E. Perrin, E.D. Rekai, and P. Sinaÿ, Synlett 420 (1994).
B. Giese, K.S. Gröninger, T. Witzel, H.G. Korth, and R. Sustmann, Angew. Chem. Int. Ed. Engl., 26, 233 (1987).
C. Taillefumier and Y. Chapleur, Chem. Rev. 104, 263 (2004).
K. Bischofberger, R.H. Hall, and A.J. Jordaan, Chem. Soc. Chem. Commun. 806 (1975).
R.H. Hall, K. Bischofberger, S.J. Eitelman, and A.J. Jordaan, Chem. Soc. Perkin Trans. 1, 743 (1977).
Y. Chapleur J. Chem. Soc. Chem. Commun. 449 (1984).
C.S. Wilcox, G.W. Long, and H. Suh, Tetrahedron Lett. 25, 395 (1984).
M. Brockhaus and J. Lehmann, Carbohydr. Res. 53, 21 (1977).
S.J. Eitelman, R.H. Hall, and A.J. Jordaan, Chem. Soc., Chem. Commun. 923 (1976).
F.K. Griffin, D.E. Paterson, P.V. Murphy, and R.J.K. Taylor, Eur. J. Org. Chem. 1305 (2002).
M. Toth and L. Somsak, J. Chem. Soc., Perkin Trans. 1, 942 (2001).
L. Lay, F. Nicotra, L. Panza, G. Russo, E. Caneva, J. Org. Chem. 57, 1304 (1992).
X. Li, H. Takahasi, H. Ohtake, and S. Ikegami, Tetrahedron Lett, 45, 3981 (2004).
G. Casiraghi, F. Zanardi, G. Rassu, and P. Spanu, Chem. Rev. 95, 1677 (1995).
B. Vauzeilles, D. Cravo, J.-M. Mallet, and P. Sinaÿ, Synlett, 522 (1993).
A.J. Fairbanks, E. Perrin, and P. Sinaÿ, Synlett 679 (1996).
D.S.T. Mazeas, O. Doumeix, J.-M. Beau, Angew. Chem. Int. Ed. Engl. 33, 1383 (1994).
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(2007). C-Glycosides. In: Synthesis and Characterization of Glycosides. Springer, Boston, MA. https://doi.org/10.1007/978-0-387-70792-1_5
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