Unified strategy for the synthesis of C-aryl glycosides

Pure and Applied Chemistry

Volumn 75, Issue 1, 2003, Pages 63-70

  Martin, Stephen F ^a  

^a The University of Texas at Austin   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 NAPHTHOL; DIHYDRONAPHTHOL; FURAN; GALTAMYCINONE; GLYCOSIDE; KETONE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

CATALYSIS; CONFERENCE PAPER; CYCLOADDITION; OXIDATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0037223535     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac200375010063     Document Type: Conference Paper

References (30)

1. For reviews of C-glycosides, see: (a) C. Jaramillo and S. Knapp. "Synthesis of C-aryl glycosides", Synthesis 1 (1993); (b) D. E. Levy and C. Tang, in The Chemistry of C-Glycosides, Elsevier Science, Tarrytown, NY (1995); (c) M. H. D. Postema, in C-Glycoside Synthesis, C. W. Rees, (Ed.), CRC Press, Boca Raton, FL (1995); (d) F. Nicotra. Top. Curr. Chem. 187, 44 (1997); (e) Y. Du and R. J. Linhardt. Tetrahedron 54, 9913 (1998).
2. For reviews of C-glycosides, see: (a) C. Jaramillo and S. Knapp. "Synthesis of C-aryl glycosides", Synthesis 1 (1993); (b) D. E. Levy and C. Tang, in The Chemistry of C-Glycosides, Elsevier Science, Tarrytown, NY (1995); (c) M. H. D. Postema, in C-Glycoside Synthesis, C. W. Rees, (Ed.), CRC Press, Boca Raton, FL (1995); (d) F. Nicotra. Top. Curr. Chem. 187, 44 (1997); (e) Y. Du and R. J. Linhardt. Tetrahedron 54, 9913 (1998).
3. For reviews of C-glycosides, see: (a) C. Jaramillo and S. Knapp. "Synthesis of C-aryl glycosides", Synthesis 1 (1993); (b) D. E. Levy and C. Tang, in The Chemistry of C-Glycosides, Elsevier Science, Tarrytown, NY (1995); (c) M. H. D. Postema, in C-Glycoside Synthesis, C. W. Rees, (Ed.), CRC Press, Boca Raton, FL (1995); (d) F. Nicotra. Top. Curr. Chem. 187, 44 (1997); (e) Y. Du and R. J. Linhardt. Tetrahedron 54, 9913 (1998).
4. For reviews of C-glycosides, see: (a) C. Jaramillo and S. Knapp. "Synthesis of C-aryl glycosides", Synthesis 1 (1993); (b) D. E. Levy and C. Tang, in The Chemistry of C-Glycosides, Elsevier Science, Tarrytown, NY (1995); (c) M. H. D. Postema, in C-Glycoside Synthesis, C. W. Rees, (Ed.), CRC Press, Boca Raton, FL (1995); (d) F. Nicotra. Top. Curr. Chem. 187, 44 (1997); (e) Y. Du and R. J. Linhardt. Tetrahedron 54, 9913 (1998).
5. For reviews of C-glycosides, see: (a) C. Jaramillo and S. Knapp. "Synthesis of C-aryl glycosides", Synthesis 1 (1993); (b) D. E. Levy and C. Tang, in The Chemistry of C-Glycosides, Elsevier Science, Tarrytown, NY (1995); (c) M. H. D. Postema, in C-Glycoside Synthesis, C. W. Rees, (Ed.), CRC Press, Boca Raton, FL (1995); (d) F. Nicotra. Top. Curr. Chem. 187, 44 (1997); (e) Y. Du and R. J. Linhardt. Tetrahedron 54, 9913 (1998).
6. K. A. Parker. Pure Appl. Chem. 66, 2135 (1994).
7. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
8. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
9. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
10. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
11. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
12. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
13. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
14. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
15. For selected references to C-aryl glycoside synthesis, see: (a) T. Hosoya, E. Takashiro, T. Matsumoto, K. Suzuki. J. Am. Chem. Soc. 116, 1004 (1994); (b) K. A. Parker and Y. H. Koh. J. Am. Chem. Soc. 116, 11149 (1994); (c) K. Toshima, G. Matsuo, T. Ishizuka, Y. Ushiki, M. Nakata, S. Matsumura. J. Org. Chem. 63, 2307 (1998); (d) C. Fuganti and S. Serra. Synlett 1241 (1999); (e) S. Futagami, Y. Ohashi, K. Imura, T. Hosoya, K. Ohmori, T. Matsumoto, K. Suzuki. Tetrahedron Lett. 41, 1063 (2000); (f) B. Schmidt. Org. Lett. 2, 791 (2000); (g) J. Rammnauth, O. Poulin, S. Rakhit, S. P. Maddaford. Org. Lett. 3, 2013 (2001); (h) M. A. Brimble and T. J. Brenstrum. J. Chem. Soc., Perkin Trans. 1 1624 (2001); (i) F. M. Hauser and X. Hu. Org. Lett. 4, 977 (2002).
16. For reviews, see: (a) P. Chiu and M. Lautens. Top. Curr. Chem. 190, 3 (1997);
17. (b) S. Woo and B. A. Keay. Synthesis 669 (1996).
18. (a) J.-P. Duan and C.-H. Cheng. Tetrahedron Lett. 34, 4019 (1993);
19. (b) C. Moinet and J.-C. Fiaud. Tetrahedron Lett. 36, 2051 (1995);
20. (c) C.-C. Feng, M. Nandi, T. Sambaiah, C.-H. Cheng. J. Org. Chem. 64, 3538 (1999).
21. D. E. Kaelin, Jr., O. D. Lopez, S. F. Martin. J. Am. Chem. Soc. 123, 6937 (2001).
22. G. Grynkiewicz and J. N. BeMiller. Carbohydr. Res. 131, 273 (1984).
23. V. A. Boyd, B. E. Drake, G. A. Sulikowski. J. Org. Chem. 58, 3191 (1993).
24. R. W. Friesen, R. W. Loo, C. F. Sturino. Can. J. Chem. 72, 1262 (1994).
25. E. Dubois and J.-M. Beau. Carbohydr. Res. 228, 103 (1992).
26. T. Matsumoto, H. Yamaguchi, K. Suzuki. Tetrahedron 53, 16533 (1997).
27. Y. Tamura, F. Fukata, M. Sasho, T. Tsugoshi, Y. Kita. J. Org. Chem. 50, 2273 (1985).
28. C. Zagar and H.-D. Scharf. Liebigs Ann. Chem. 447 (1993).
29. R. L. Hannan, R. B. Barber, H. Rapoport. J. Org. Chem. 44, 2153 (1979).
30. A. J. Pihko, K. C. Nicolaou, A. M. P. Koskinen. Tetrahedron: Asymmetry 12, 937 (2001).