Synthesis of 4,4-difluoroglycosides using ring-closing metathesis

Organic and Biomolecular Chemistry

Volumn 2, Issue 4, 2004, Pages 528-541

  Audouard, Christophe ^a   Fawcett, John ^a   Griffiths, Gerry A ^a   Percy, Jonathan M ^a   Pintat, Stéphane ^a,c   Smith, Clive A ^b  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

^c Eyotech OAI   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ANTIBIOTICS; CHEMICAL BONDS; CHROMATOGRAPHIC ANALYSIS; CONFORMATIONS; FLUORINE; OLEFINS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); WATER;

FLUOROSUGARS; RING-CLOSING METATHESIS;

SUGARS;

FLUORINE DERIVATIVE; GLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

FLUORINE COMPOUNDS; GLYCOSIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE;

EID: 1342281357     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b313731g     Document Type: Article

References (69)

1. M. N. Namchuk, J. D. McCarter, A. Becalski, T. Andrews and S. G. Withers, J. Am. Chem. Soc., 2000, 122, 1270-1277.
2. M. Namchuk, C. Braun, J. D. McCarter and S. G. Withers, ACS Symp. Ser., 1996, 639, 279-293. For 5-fluoroglycoside analogues, see: S. Howard, S. M. He and S. G. Withers, J. Biol. Chem., 1998, 273, 2067-2072; M. C. T. Hartman and J. K. Coward, J. Am. Chem. Soc., 2002, 124, 10036-10053.
3. M. Namchuk, C. Braun, J. D. McCarter and S. G. Withers, ACS Symp. Ser., 1996, 639, 279-293. For 5-fluoroglycoside analogues, see: S. Howard, S. M. He and S. G. Withers, J. Biol. Chem., 1998, 273, 2067-2072; M. C. T. Hartman and J. K. Coward, J. Am. Chem. Soc., 2002, 124, 10036-10053.
4. M. Namchuk, C. Braun, J. D. McCarter and S. G. Withers, ACS Symp. Ser., 1996, 639, 279-293. For 5-fluoroglycoside analogues, see: S. Howard, S. M. He and S. G. Withers, J. Biol. Chem., 1998, 273, 2067-2072; M. C. T. Hartman and J. K. Coward, J. Am. Chem. Soc., 2002, 124, 10036-10053.
5. G. Sulzenbacher, L. F. Mackenzie, K. S. Wilson, S. G. Withers, C. Dupont and G. J. Davies, Biochemistry, 1999, 38, 4826-4833; K. Persson, H. D. Ly, M. Dieckelmann, W. W Wakarchuk, S. G. Withers and N. C. J. Strynadka, Nat. Struct. Biol., 2001, 8, 166-175; V. M.-A. Ducros, D. L. Zechel, G. N. Murshudov, H. J. Gilbert, L. Szabó, D. Stoll and S. G. Withers, Angew. Chem., Int. Ed., 2002, 41, 2824-2827.
6. G. Sulzenbacher, L. F. Mackenzie, K. S. Wilson, S. G. Withers, C. Dupont and G. J. Davies, Biochemistry, 1999, 38, 4826-4833; K. Persson, H. D. Ly, M. Dieckelmann, W. W Wakarchuk, S. G. Withers and N. C. J. Strynadka, Nat. Struct. Biol., 2001, 8, 166-175; V. M.-A. Ducros, D. L. Zechel, G. N. Murshudov, H. J. Gilbert, L. Szabó, D. Stoll and S. G. Withers, Angew. Chem., Int. Ed., 2002, 41, 2824-2827.
7. G. Sulzenbacher, L. F. Mackenzie, K. S. Wilson, S. G. Withers, C. Dupont and G. J. Davies, Biochemistry, 1999, 38, 4826-4833; K. Persson, H. D. Ly, M. Dieckelmann, W. W Wakarchuk, S. G. Withers and N. C. J. Strynadka, Nat. Struct. Biol., 2001, 8, 166-175; V. M.-A. Ducros, D. L. Zechel, G. N. Murshudov, H. J. Gilbert, L. Szabó, D. Stoll and S. G. Withers, Angew. Chem., Int. Ed., 2002, 41, 2824-2827.
8. D. O. Hart, S. M. He, C. J. Chany, S. G. Withers, P. F. G. Sims, M. L. Sinnott and H. Brumer, Biochemistry, 2000, 39, 98269836.
9. S. P. Vincent, M. D. Burkart, C. Y Tsai, Z. Y. Zhang and C. H. Wong, J. Org. Chem., 1999, 64, 5264-5279.
10. S. G. Withers. M. D. Percival and I. P. Street, Carbohydr. Res., 1989, 187, 43-66.
11. K. Dax, M. Albert, J. Ortner and B. J. Paul, Carbohydr. Res., 2000, 327, 47-86; K. Dax and M. Albert, Top. Curr. Chem., 2001, 215, 193-275.
12. K. Dax, M. Albert, J. Ortner and B. J. Paul, Carbohydr. Res., 2000, 327, 47-86; K. Dax and M. Albert, Top. Curr. Chem., 2001, 215, 193-275.
13. A. Ellaghdach, R. Echarri, M. I. Matheu, M. I. Barrena, S. Castillon and J. Garcia, J. Org. Chem., 1991, 56, 4556-4559; R. Fernandez, M. I. Matheu, R. Echarri and S. Castillon, Tetrahedron, 1998, 54, 3523-3532; M. I. Barrena, M. I. Matheu and S. Castillon, J. Org. Chem., 1998, 63, 2184-2188; R. Fernandez and S. Castillon, Tetrahedron, 1999, 55, 8497-85081; M. L. Aghmiz, Y. Diaz, G. H. Jana, M. I. Matheu, R. Echarri, S. Castillon and M. L. Jimeno, Tetrahedron, 2001, 57, 6733-6743.
14. A. Ellaghdach, R. Echarri, M. I. Matheu, M. I. Barrena, S. Castillon and J. Garcia, J. Org. Chem., 1991, 56, 4556-4559; R. Fernandez, M. I. Matheu, R. Echarri and S. Castillon, Tetrahedron, 1998, 54, 3523-3532; M. I. Barrena, M. I. Matheu and S. Castillon, J. Org. Chem., 1998, 63, 2184-2188; R. Fernandez and S. Castillon, Tetrahedron, 1999, 55, 8497-85081; M. L. Aghmiz, Y. Diaz, G. H. Jana, M. I. Matheu, R. Echarri, S. Castillon and M. L. Jimeno, Tetrahedron, 2001, 57, 6733-6743.
15. A. Ellaghdach, R. Echarri, M. I. Matheu, M. I. Barrena, S. Castillon and J. Garcia, J. Org. Chem., 1991, 56, 4556-4559; R. Fernandez, M. I. Matheu, R. Echarri and S. Castillon, Tetrahedron, 1998, 54, 3523-3532; M. I. Barrena, M. I. Matheu and S. Castillon, J. Org. Chem., 1998, 63, 2184-2188; R. Fernandez and S. Castillon, Tetrahedron, 1999, 55, 8497-85081; M. L. Aghmiz, Y. Diaz, G. H. Jana, M. I. Matheu, R. Echarri, S. Castillon and M. L. Jimeno, Tetrahedron, 2001, 57, 6733-6743.
16. A. Ellaghdach, R. Echarri, M. I. Matheu, M. I. Barrena, S. Castillon and J. Garcia, J. Org. Chem., 1991, 56, 4556-4559; R. Fernandez, M. I. Matheu, R. Echarri and S. Castillon, Tetrahedron, 1998, 54, 3523-3532; M. I. Barrena, M. I. Matheu and S. Castillon, J. Org. Chem., 1998, 63, 2184-2188; R. Fernandez and S. Castillon, Tetrahedron, 1999, 55, 8497-85081; M. L. Aghmiz, Y. Diaz, G. H. Jana, M. I. Matheu, R. Echarri, S. Castillon and M. L. Jimeno, Tetrahedron, 2001, 57, 6733-6743.
17. A. Ellaghdach, R. Echarri, M. I. Matheu, M. I. Barrena, S. Castillon and J. Garcia, J. Org. Chem., 1991, 56, 4556-4559; R. Fernandez, M. I. Matheu, R. Echarri and S. Castillon, Tetrahedron, 1998, 54, 3523-3532; M. I. Barrena, M. I. Matheu and S. Castillon, J. Org. Chem., 1998, 63, 2184-2188; R. Fernandez and S. Castillon, Tetrahedron, 1999, 55, 8497-85081; M. L. Aghmiz, Y. Diaz, G. H. Jana, M. I. Matheu, R. Echarri, S. Castillon and M. L. Jimeno, Tetrahedron, 2001, 57, 6733-6743.
18. H. W. Chen, Z. B. Zhao, T. M. Hallis, Z. H. Guo and H. W. Liu, Angew. Chem., Int. Ed., 2001, 40, 607-610. For the synthesis of a difluorinated anyhdrosugar related to our targets, see: F. Oberdorfer, R. Haeckel and G. Lauer, Synthesis, 1998, 201-206. The synthesis is based upon a low yielding reaction of D-galactal, and an inefficient fluorination with DAST.
19. H. W. Chen, Z. B. Zhao, T. M. Hallis, Z. H. Guo and H. W. Liu, Angew. Chem., Int. Ed., 2001, 40, 607-610. For the synthesis of a difluorinated anyhdrosugar related to our targets, see: F. Oberdorfer, R. Haeckel and G. Lauer, Synthesis, 1998, 201-206. The synthesis is based upon a low yielding reaction of D-galactal, and an inefficient fluorination with DAST.
20. S. Gaisser, C. J. Martin, B. Wilkinson, R. M. Sheridan, R. E. Lill, A. J. Weston, S. J. Ready, C. Waldron, G. D. Crouse, P. F. Leadlay and J. Staunton, Chem. Commun., 2002, 618-619 explicitly raises the issue of conformational flexibility in highly deoxygenated sugars, and the relationship to specificity of biosynthetic enzymes.
21. U. M. Unligil and J. M. Rini, Curr. Opin. Struct. Biol., 2000, 10, 510-517. For recent theroetical work, see: I. Tvaroska, I. Andre and J. P. Carver, J. Am. Chem. Soc., 2000, 122, 8762-8776.
22. U. M. Unligil and J. M. Rini, Curr. Opin. Struct. Biol., 2000, 10, 510-517. For recent theroetical work, see: I. Tvaroska, I. Andre and J. P. Carver, J. Am. Chem. Soc., 2000, 122, 8762-8776.
23. T. Taguchi, Y. Kodama and M. Kanazawa, Carbohydr. Res., 1993, 249, 243-252.
24. H. Amii, T. Kobayashi, H. Terasawa and K. Uneyama, Org. Lett., 2001, 3, 3103-3105.
25. J. M. Percy and S. Pintat, Chem. Commun., 2000, 607-608.
26. D. Seyferth, R. M. Simon, D. J. Sepelak and H. A. Klein, J. Am. Chem. Soc., 1983, 105, 4634-4639.
27. Z. Y. Yang and D. J. Burton, J. Org. Chem., 1991, 56, 1037-1041.
28. M. Kirihara, T. Takuwa, S. Takizawa, T. Momose and H. Nemoto, Tetrahedron, 2000, 56, 8275-8280. For reactions of related building blocks, see : Z. G. Wang and G. B. Hammond, Chem. Commun., 1999, 2545-2546; Z. G. Wang and G. B. Hammond, Tetrahedron Lett., 2000, 41, 2339-2342; Y. Hanzawa, K. Inazawa, A. Kon, H. Aoki and Y. Kobayashi, Tetrahedron Lett., 1987, 28, 659-662. For a recent difluoronucleoside synthesis using 1-bromo-1, 1difluoropropene, see: X. G. Zhang, H. R. Xi, X. C. Dong, J. Jin, W. D. Meng and F. L. Qing, J. Org. Chem., 2003, 68, 9026-9033.
29. M. Kirihara, T. Takuwa, S. Takizawa, T. Momose and H. Nemoto, Tetrahedron, 2000, 56, 8275-8280. For reactions of related building blocks, see : Z. G. Wang and G. B. Hammond, Chem. Commun., 1999, 2545-2546; Z. G. Wang and G. B. Hammond, Tetrahedron Lett., 2000, 41, 2339-2342; Y. Hanzawa, K. Inazawa, A. Kon, H. Aoki and Y. Kobayashi, Tetrahedron Lett., 1987, 28, 659-662. For a recent difluoronucleoside synthesis using 1-bromo-1, 1difluoropropene, see: X. G. Zhang, H. R. Xi, X. C. Dong, J. Jin, W. D. Meng and F. L. Qing, J. Org. Chem., 2003, 68, 9026-9033.
30. M. Kirihara, T. Takuwa, S. Takizawa, T. Momose and H. Nemoto, Tetrahedron, 2000, 56, 8275-8280. For reactions of related building blocks, see : Z. G. Wang and G. B. Hammond, Chem. Commun., 1999, 2545-2546; Z. G. Wang and G. B. Hammond, Tetrahedron Lett., 2000, 41, 2339-2342; Y. Hanzawa, K. Inazawa, A. Kon, H. Aoki and Y. Kobayashi, Tetrahedron Lett., 1987, 28, 659-662. For a recent difluoronucleoside synthesis using 1-bromo-1, 1difluoropropene, see: X. G. Zhang, H. R. Xi, X. C. Dong, J. Jin, W. D. Meng and F. L. Qing, J. Org. Chem., 2003, 68, 9026-9033.
31. M. Kirihara, T. Takuwa, S. Takizawa, T. Momose and H. Nemoto, Tetrahedron, 2000, 56, 8275-8280. For reactions of related building blocks, see : Z. G. Wang and G. B. Hammond, Chem. Commun., 1999, 2545-2546; Z. G. Wang and G. B. Hammond, Tetrahedron Lett., 2000, 41, 2339-2342; Y. Hanzawa, K. Inazawa, A. Kon, H. Aoki and Y. Kobayashi, Tetrahedron Lett., 1987, 28, 659-662. For a recent difluoronucleoside synthesis using 1-bromo-1, 1difluoropropene, see: X. G. Zhang, H. R. Xi, X. C. Dong, J. Jin, W. D. Meng and F. L. Qing, J. Org. Chem., 2003, 68, 9026-9033.
32. M. Kirihara, T. Takuwa, S. Takizawa, T. Momose and H. Nemoto, Tetrahedron, 2000, 56, 8275-8280. For reactions of related building blocks, see : Z. G. Wang and G. B. Hammond, Chem. Commun., 1999, 2545-2546; Z. G. Wang and G. B. Hammond, Tetrahedron Lett., 2000, 41, 2339-2342; Y. Hanzawa, K. Inazawa, A. Kon, H. Aoki and Y. Kobayashi, Tetrahedron Lett., 1987, 28, 659-662. For a recent difluoronucleoside synthesis using 1-bromo-1, 1difluoropropene, see: X. G. Zhang, H. R. Xi, X. C. Dong, J. Jin, W. D. Meng and F. L. Qing, J. Org. Chem., 2003, 68, 9026-9033.
33. M. Schlosser and S. Strunk, Tetrahedron, 1989, 45, 2649-2664; S. T. Patel, J. M. Percy and R. D. Wilkes, J. Org. Chem., 1996, 61, 166-173.
34. M. Schlosser and S. Strunk, Tetrahedron, 1989, 45, 2649-2664; S. T. Patel, J. M. Percy and R. D. Wilkes, J. Org. Chem., 1996, 61, 166-173.
35. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., Int. Ed. Engl, 1995, 34, 2039-2041.
36. M. Ahmed, A. G. M. Barrett, D. C. Braddock, S. M. Cramp and P. A. Procopiou, Tetrahedron Lett., 1999, 40, 8657-8662.
37. J. A. Marco, M. Carda, S. Rodriguez, E. Castillo and M. N. Kneeteman, Tetrahedron, 2003, 59, 4085-4101.
38. L. Ackermann, A. Furstner, T. Weskamp, F. J. Kohl and W. A. Herrmann, Tetrahedron Lett., 1999, 40, 4787-4790; J. K. Huang, E. D. Stevens. S. P. Nolan and J. L. Petersen, J. Am. Chem. Soc., 1999, 121, 2674-2678; M. Scholl, T. M. Trnka, J. P. Morgan and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 2247-2250.
39. L. Ackermann, A. Furstner, T. Weskamp, F. J. Kohl and W. A. Herrmann, Tetrahedron Lett., 1999, 40, 4787-4790; J. K. Huang, E. D. Stevens. S. P. Nolan and J. L. Petersen, J. Am. Chem. Soc., 1999, 121, 2674-2678; M. Scholl, T. M. Trnka, J. P. Morgan and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 2247-2250.
40. L. Ackermann, A. Furstner, T. Weskamp, F. J. Kohl and W. A. Herrmann, Tetrahedron Lett., 1999, 40, 4787-4790; J. K. Huang, E. D. Stevens. S. P. Nolan and J. L. Petersen, J. Am. Chem. Soc., 1999, 121, 2674-2678; M. Scholl, T. M. Trnka, J. P. Morgan and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 2247-2250.
41. V. S. Enev, H. Kaehlig and J. Mulzer, J. Am. Chem. Soc., 2001, 123, 10764-10765.
42. V. VanRheenen, R. C. Kelly and D. Y. Cha, Tetrahedron Lett., 1976, 1973-1976.
43. K. T. Tan, S. S. Chng, H. S. Cheng and T. P. Loh, J. Am. Chem. Soc., 2003, 125, 2958-2963.
44. L. A. Paquette, Synthesis, 2003, 765-774.
45. J. K. Cha and N. S. Kim, Chem. Rev., 1995, 95, 1761-1795.
46. H. W. Kim, P. Rossi, R. K. Shoemaker and S. G. DiMagno, J. Am. Chem. Soc., 1998, 120, 9082-9083.
47. For an extensive recent compilation of relevant NMR data, including long-range H-F coupling constants, see: M. Michalik, M. Hein and M. Frank, Carbohydr. Res., 2000, 327, 185-218.
48. P. Collins and M. Ferrier, Monosaccharides: Their Chemistry, and Their Roles in Natural Products, Wiley, Chichester, 1995, 40-44. Clearly furanose forms are unavailable to 32 because there is no hydroxyl group at C-4.
49. M. de Rosa, A. Solladie-Cavallo and A. Scettri, Tetrahedron Lett., 2000, 41, 1593-1596.
50. M. T. Crimmins and A. L. Choy, J. Org. Chem., 1997, 62, 7548-7549.
51. C. Held, R. Fröhlich and P. Metz, Angew. Chem., Int. Ed. Engl., 2001, 40, 1058-1060.
52. F. Rutjes, T. M. Kooistra, H. Hiemstra and H. E. Schoemaker, Synlett, 1998, 192-194.
53. M. T. Crimmins and B. W. King, J. Am. Chem. Soc., 1998, 120, 9084-9085.
54. G. T. Nadolski and B. S. Davidson, Tetrahedron Lett., 2001, 42, 797-800.
55. P. V. Ramachandran, M. V. R. Reddy and H. C. Brown, Tetrahedron Lett., 2000, 41, 583-586.
56. A. Kirby, 'The Anomeric Effect, and Related Stereoelectronic Effects at Oxygen', Springer-Verlag, Berlin, 1983, pp. 72-75.
57. A. J. Clark, Chem. Soc. Rev., 2002, 31, 1-11 discusses many of these, and related issues.
58. G. Stork, R. Mook, S. A. Biller and S. D. Rychnovsky, J. Am. Chem. Soc., 1983, 105, 3741-3742.
59. T. Itoh, K. Sakabe, K. Kudo, H. Ohara, Y. Takagi, H. Kihara, P. Zagatti and M. Renou, J. Org. Chem., 1999, 64, 252-265. For related cyclisations of difluoroamides see : H. Nagashima, Y. Isono and S. Iwamatsu, J. Org. Chem., 2001, 66, 315-319. The conformational preference in amides is considerably less well defined, as discussed in ref. 38, p. 114, meaning that amides can be cyclised at that oxidation level, and do not require reduction to the aminals.
60. T. Itoh, K. Sakabe, K. Kudo, H. Ohara, Y. Takagi, H. Kihara, P. Zagatti and M. Renou, J. Org. Chem., 1999, 64, 252-265. For related cyclisations of difluoroamides see : H. Nagashima, Y. Isono and S. Iwamatsu, J. Org. Chem., 2001, 66, 315-319. The conformational preference in amides is considerably less well defined, as discussed in ref. 38, p. 114, meaning that amides can be cyclised at that oxidation level, and do not require reduction to the aminals.
61. T. R. Hoye and H. Zhao, Org. Lett., 1999, 1, 1123-1125.
62. D. J. O'Leary, H. E. Blackwell, R. A. Washenfelder, K. Miura and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 1091-1094. See also: D. J. O'Leary, H. E. Blackwell, R. A. Washenfelder and R. H. Grubbs, Tetrahedron Lett., 1998, 39, 7427-7430.
63. D. J. O'Leary, H. E. Blackwell, R. A. Washenfelder, K. Miura and R. H. Grubbs, Tetrahedron Lett., 1999, 40, 1091-1094. See also: D. J. O'Leary, H. E. Blackwell, R. A. Washenfelder and R. H. Grubbs, Tetrahedron Lett., 1998, 39, 7427-7430.
64. A. K. Chatterjee, J. P. Morgan, M. Scholl and R. H. Grubbs, J. Am. Chem. Soc.. 2000, 122, 3783-3784 raises may issues relevant to this study. For a review of mechanistic work in the area, see : T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18-29. For an excellent recent review of factors influencing selectivity in cross-metathesis, see: A. K. Chatterjee, T.-L. Choi, D. P. Sanders and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360-11370.
65. A. K. Chatterjee, J. P. Morgan, M. Scholl and R. H. Grubbs, J. Am. Chem. Soc.. 2000, 122, 3783-3784 raises may issues relevant to this study. For a review of mechanistic work in the area, see : T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18-29. For an excellent recent review of factors influencing selectivity in cross-metathesis, see: A. K. Chatterjee, T.-L. Choi, D. P. Sanders and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360-11370.
66. A. K. Chatterjee, J. P. Morgan, M. Scholl and R. H. Grubbs, J. Am. Chem. Soc.. 2000, 122, 3783-3784 raises may issues relevant to this study. For a review of mechanistic work in the area, see : T. M. Trnka and R. H. Grubbs, Acc. Chem. Res., 2001, 34, 18-29. For an excellent recent review of factors influencing selectivity in cross-metathesis, see: A. K. Chatterjee, T.-L. Choi, D. P. Sanders and R. H. Grubbs, J. Am. Chem. Soc., 2003, 125, 11360-11370.
67. S. Imhof, S. Randl and S. Blechert, Chem. Commun., 2001, 1692-1693.
68. T. M. Trnka, M. W. Day and R. H. Grubbs, Angew. Chem., Int. Ed. Engl., 2001, 40, 3441-3444.
69. D. V. McGrath and R. H. Grubbs, Organometallics, 1994, 13, 224-235.