Expeditious entry to C-alkyl and C-aryl pyranoid glycals: Reaction of anomeric glycosyl chlorides with organolithiums

Chemical Communications

Volumn , Issue 20, 1996, Pages 2357-2358

  Gómez, Ana M ^a   Casillas, Marta ^a   Valverde, Serafin ^a   López, J Cristóbal ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002059047     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960002357     Document Type: Article

References (41)

1. Reviews: M. H. D. Postema, in C-Glycoside Synthesis, ed. C. W. Rees, CRC Press, Boca Raton, FL, 1995; M. H. D. Postema, Tetrahedron, 1992, 48, 8545; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 1983, 9, 415; S. Hanessian and A. G. Pernet, Adv. Carbohydr. Chem. Biochem., 1976, 33, 111.
2. Reviews: M. H. D. Postema, in C-Glycoside Synthesis, ed. C. W. Rees, CRC Press, Boca Raton, FL, 1995; M. H. D. Postema, Tetrahedron, 1992, 48, 8545; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 1983, 9, 415; S. Hanessian and A. G. Pernet, Adv. Carbohydr. Chem. Biochem., 1976, 33, 111.
3. Reviews: M. H. D. Postema, in C-Glycoside Synthesis, ed. C. W. Rees, CRC Press, Boca Raton, FL, 1995; M. H. D. Postema, Tetrahedron, 1992, 48, 8545; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 1983, 9, 415; S. Hanessian and A. G. Pernet, Adv. Carbohydr. Chem. Biochem., 1976, 33, 111.
4. Reviews: M. H. D. Postema, in C-Glycoside Synthesis, ed. C. W. Rees, CRC Press, Boca Raton, FL, 1995; M. H. D. Postema, Tetrahedron, 1992, 48, 8545; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 1983, 9, 415; S. Hanessian and A. G. Pernet, Adv. Carbohydr. Chem. Biochem., 1976, 33, 111.
5. K. C. Nicolaou, C.-K. Hwang and M. E. Duggan, J. Chem. Soc., Chem. Commun., 1986, 925.
6. S. Hanessian, M. Martin and R. C. Desai, J. Chem. Soc., Chem. Commun., 1986, 926.
7. P. Lesimple, J.-M. Beau, G. Jaurand and P. Sinaÿ, Tetrahedron Lett., 1986, 27, 6201; J. Prandi, C. Audin and J.-M. Beau, Tetrahedron Lett., 1991, 32, 769.
8. P. Lesimple, J.-M. Beau, G. Jaurand and P. Sinaÿ, Tetrahedron Lett., 1986, 27, 6201; J. Prandi, C. Audin and J.-M. Beau, Tetrahedron Lett., 1991, 32, 769.
9. R. R. Schmidt, R. Preuss and R. Betz, Tetrahedron Lett., 1987, 28, 6591.
10. (a) K. A. Parker and D.-S. Su, J. Org. Chem., 1996, 61, 2191;
11. (b) K. A. Parker, C. A. Coburn and Y.-h. Koh, J. Org. Chem., 1995, 60, 2938;
12. (c) K. A. Parker and Y.-h. Koh, J. Am. Chem Soc., 1994, 116, 11149;
13. (d) K. A. Parker, Pure Appl. Chem., 1994, 66, 2135;
14. (e) K. A. Parker and C. A. Coburn, J. Org. Chem., 1992, 57, 5547;
15. (f) K. A. Parker and C. A. Coburn, J. Org. Chem., 1991, 113, 8516.
16. (a) E. Dubois and J.-M. Beau, Carbohydr. Res., 1992, 228, 103;
17. (b) E. Dubois and J.-M. Beau, Tetrahedron Lett., 1990, 31, 5165;
18. c) E. Dubois and J.-M. Beau, J. Chem. Soc., Chem. Commun., 1990, 1191.
19. M. A. Tius, J. Gomez-Galeno, X.-q. Gu and J. H. Zaidi, J. Am. Chem. Soc., 1991, 113, 5775; M. A. Tius, X.-q. Gu and J. Gomez-Galeno, J. Am. Chem. Soc., 1990, 112, 8188.
20. M. A. Tius, J. Gomez-Galeno, X.-q. Gu and J. H. Zaidi, J. Am. Chem. Soc., 1991, 113, 5775; M. A. Tius, X.-q. Gu and J. Gomez-Galeno, J. Am. Chem. Soc., 1990, 112, 8188.
21. (a) R. W. Friesen, R. W. Loo and C. F. Sturino, Can. J. Chem., 1994, 72, 1262;
22. (b) R. W. Friesen, C. F. Sturino, A. K. Daljeet and A. Kolaczewska, J. Org. Chem., 1991, 56, 1944;
23. (c) R. W. Friesen and A. K. Daljeet, Tetrahedron Lett., 1990, 31, 6133;
24. (d) R. W. Friesen and C. F. Sturino, J. Org. Chem., 1990, 55, 5808;
25. (e) R. W. Friesen and C. F. Sturino, J. Org. Chem., 1990, 55, 2572.
26. C. Barber, K. Jarowicki and P. Kocienski, Synlett, 1991, 197.
27. V. A. Boyd, B. E. Drake and G. A. Sulikowski, J. Org. Chem., 1993, 58, 3191.
28. Reviews: (a) K. Suzuki and T. Matsumoto, in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, ed. G. Lukacs, Springer-Verlag: Berlin, 1993, vol. 2, pp. 352-403; (b) K. Suzuki, Pure Appl. Chem., 1994, 66, 2175; (c) C. Jaramillo and S. Knapp, Synthesis, 1994, 1 and references cited therein.
29. Reviews: (a) K. Suzuki and T. Matsumoto, in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, ed. G. Lukacs, Springer-Verlag: Berlin, 1993, vol. 2, pp. 352-403; (b) K. Suzuki, Pure Appl. Chem., 1994, 66, 2175; (c) C. Jaramillo and S. Knapp, Synthesis, 1994, 1 and references cited therein.
30. Reviews: (a) K. Suzuki and T. Matsumoto, in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, ed. G. Lukacs, Springer-Verlag: Berlin, 1993, vol. 2, pp. 352-403; (b) K. Suzuki, Pure Appl. Chem., 1994, 66, 2175; (c) C. Jaramillo and S. Knapp, Synthesis, 1994, 1 and references cited therein.
31. U. Hacksell and G. D. Daves Jr., Prog. Med. Chem., 1985, 22, 1.
32. M. Casillas, A. M. Gómez, J. C. López and S. Valverde, Synlett, 1996, 628.
33. R. E. Ireland, S. Thaisrivongs, N. Vanier and C. S. Wilcox, J. Org. Chem., 1980, 45, 48.
34. K. Takeo, M. Nakagen, Y. Teramoto and Y. Nitta, Carbohydr. Res., 1990, 201, 261.
35. S. Harusawa, M. Kawabata, Y. Murai, R. Yoneda and T. Kurihara, Chem. Pharm. Bull., 1995, 43, 152.
36. C. D. Hurd and R. P. Holysz, J. Am. Chem. Soc., 1950, 72, 1735; C. D. Hurd and H. T. Miles, J. Org. Chem., 1964, 29, 2976; R. Shapiro, J. Am. Chem. Soc., 1961, 83, 3920; R. Bihovsky, C. Selick and I. Giusti, J. Org. Chem., 1988, 53, 4026 and references cited therein.
37. C. D. Hurd and R. P. Holysz, J. Am. Chem. Soc., 1950, 72, 1735; C. D. Hurd and H. T. Miles, J. Org. Chem., 1964, 29, 2976; R. Shapiro, J. Am. Chem. Soc., 1961, 83, 3920; R. Bihovsky, C. Selick and I. Giusti, J. Org. Chem., 1988, 53, 4026 and references cited therein.
38. C. D. Hurd and R. P. Holysz, J. Am. Chem. Soc., 1950, 72, 1735; C. D. Hurd and H. T. Miles, J. Org. Chem., 1964, 29, 2976; R. Shapiro, J. Am. Chem. Soc., 1961, 83, 3920; R. Bihovsky, C. Selick and I. Giusti, J. Org. Chem., 1988, 53, 4026 and references cited therein.
39. C. D. Hurd and R. P. Holysz, J. Am. Chem. Soc., 1950, 72, 1735; C. D. Hurd and H. T. Miles, J. Org. Chem., 1964, 29, 2976; R. Shapiro, J. Am. Chem. Soc., 1961, 83, 3920; R. Bihovsky, C. Selick and I. Giusti, J. Org. Chem., 1988, 53, 4026 and references cited therein.
40. J. C. López, A. M. Gómez and B. Fraser-Reid, J. Org. Chem., 1995, 60, 3871; J. C. López and B. Fraser-Reid, J. Am. Chem. Soc., 1989, 111, 3450.
41. J. C. López, A. M. Gómez and B. Fraser-Reid, J. Org. Chem., 1995, 60, 3871; J. C. López and B. Fraser-Reid, J. Am. Chem. Soc., 1989, 111, 3450.