Synthesis of 1′,2′-cis-Nucleoside analogues: Evidence of stereoelectronic control for SN2 reactions at the anomeric center of furanosides

Journal of the American Chemical Society

Volumn 132, Issue 35, 2010, Pages 12433-12439

  Prěvost, Michel ^a,b,c   St Jean, Olivier ^a,b,c   Guindon, Yvan ^a,b,c  

^a CLIN RESEARCH INSTITUTE OF MONTREAL   (Canada)

^b UNIVERSITÉ DE MONTRÉAL   (Canada)

^c MCGILL UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERICS; DIASTEREOSELECTIVE; FIVE-MEMBERED RINGS; GLYCOSIDATIONS; LACTOLS; MEDICINAL CHEMISTRY; NUCLEOBASES; NUCLEOSIDE ANALOGUES; TRANSITION STATE;

BROMINE COMPOUNDS; SYNTHESIS (CHEMICAL);

BIOMOLECULES;

BORON DERIVATIVE; BROMIDE; NUCLEIC ACID BASE; NUCLEOSIDE ANALOG; FURAN DERIVATIVE; NUCLEOSIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSIDATION; SILYLATION; STEREOCHEMISTRY; SYNTHESIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM;

FURANS; MOLECULAR CONFORMATION; NUCLEOSIDES; STEREOISOMERISM;

EID: 77956260481     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja104429y     Document Type: Article

References (87)

1. Howell, H. G., Brodfuehrer, P. R., Brundidge, S. P., Benigni, D. A., and Sapino, C., Jr. J. Org. Chem. 1988, 53, 85
2. De Francesco, R. and Carfi, A. Adv. Drug Delivery Rev. 2007, 59, 1242
3. De Clercq, E. Med. Res. Rev. 2009, 29, 571
4. Sabini, E., Ort, S., Monnerjahn, C., Konrad, M., and Lavie, A. Nat. Struct. Biol. 2003, 10, 513
5. Otovaě, B., Hrdyě, J., Votruba, I., and Holyě, A. Anticancer Res. 2009, 29, 1295
6. De Clercq, E. Nat. Rev. Drug Discovery 2007, 6, 1001
7. Klein, R. S., Lenzi, M., Lim, T. H., Hotchkiss, K. A., Wilson, P., and Schwartz, E. L. Biochem. Pharmacol. 2001, 62, 1257
8. Rumjahn, S. M., Yokdang, N., Baldwin, K. A., Thai, J., and Buxton, I. L. O. Br. J. Cancer 2009, 100, 1465
9. Chuang, R. Y. and Chuang, L. F. Nature 1976, 260, 549
10. Bonate, P. L., Arthaud, L., Cantrell, W. R., Stephenson, K., Secrist, J. A., III, and Weitman, S. Nat. Rev. Drug Discovery 2006, 5, 855
11. Zhu, X., Kawatkar, S., Rao, Y., and Boons, G. J. J. Am. Chem. Soc. 2006, 128, 11948
12. Ness, R. K., Fletcher, H. G., Jr., and Hudson, C. S J. Am. Chem. Soc. 1950, 72, 2200
13. Niedballa, U. and Vorbrüggen, H. J. Org. Chem. 1974, 39, 3672
14. Vorbrüggen, H. and Ruh-Pohlenz, C. Handbook of Nucleoside Synthesis; John Wiley & Sons: New York: 2001.
15. Glaudemans, C. P. J. and Fletcher, H. G, Jr. J. Org. Chem. 1963, 28, 3004
16. Shen, T. Y., Lewis, H. M., and Ruyle, W. V. J. Org. Chem. 1965, 835
17. Keller, F. and Tyrrill, A. R. J. Org. Chem. 1966, 31, 1289
18. Stevens, J. D., Ness, R. K., and Fletcher, G., H J. Org. Chem. 1968, 33, 1806
19. Noyori, R. and Hayashi, M. Chem. Lett. 1987, 16, 57
20. Kadir, K., Mackenzie, G., and Shaw, G. J. Chem. Soc., Perkin Trans. 1 1980, 2304
21. Nokami, J., Osafune, M., Ito, Y., Miyake, F., Sumida, S.-i., and Torii, S. Chem. Lett. 1999, 1053
22. Crich, D., Pedersen, C. M., Bowers, A. A., and Wink, D. J. J. Org. Chem. 2007, 72, 1553
23. Mukaiyama, T., Yamada, M., Suda, S., Yokomizo, Y., and Kobayashi, K. Chem. Lett. 1992, 1401
24. Hanessian, S., Conde, J. J., and Lou, B. Tetrahedron Lett. 1995, 36, 5865
25. Kim, K. S., Fulse, D. B., Baek, J. Y., Lee, B.-Y., and Jeon, H. B. J. Am. Chem. Soc. 2008, 130, 8537
26. Sammakia, T. and Smith, R. S. J. Am. Chem. Soc. 1994, 116, 7915
27. Larsen, C. H., Ridgway, B. H., Shaw, J. T., Smith, D. M., and Woerpel, K. A. J. Am. Chem. Soc. 2005, 127, 10879
28. Streitwieser, A. and Jayasree, E. G. J. Org. Chem. 2007, 72, 1785
29. Zhang, Y., Reynolds, N. T., Manju, K., and Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720
30. Shenoy, S. R. and Woerpel, K. A. Org. Lett. 2005, 7, 1157
31. Crich, D. and Li, L. J. Org. Chem. 2007, 72, 1681
32. 2-hybridized with participation of the endocyclic oxygen to stabilize the developing positive charge. In these transition states, bond forming and bond breaking are considered to be occurring in a symmetrical manner.
33. Crich, D. and Chandrasekera, N. S. Angew. Chem., Int. Ed. 2004, 43, 5386
34. Krumper, J. R., Salamant, W. A., and Woerpel, K. A. J. Org. Chem. 2009, 74, 8039
35. Walvoort, M. T. C., Lodder, G., Mazurek, J., Overkleeft, H. S., Coděe, J. D. C., and van der Marel, G. A. J. Am. Chem. Soc. 2009, 131, 12080
36. Ichikawa, S., Hayashi, R., Hirano, S., and Matsuda, A. Org. Lett. 2008, 10, 5107
37. Yang, M. T. and Woerpel, K. A. J. Org. Chem. 2009, 74, 545
38. Dinkelaar, J., de Jong, A. R., van Meer, R., Somers, M., Lodder, G., Overkleeft, H. S., Coděe, J. D. C., and van der Marel, G. A. J. Org. Chem. 2009, 74, 4982
39. 2BI, were considered. Similar trends were observed with compound 15, but the scope of this activating agent remains to be investigated.
40. Ellervik, U. and Magnusson, G. J. Am. Chem. Soc. 1994, 116, 2340
41. Guindon, Y., Ogilvie, W. W., Bordeleau, J., Cui, W. L., Durkin, K., Gorys, V., Juteau, H., Lemieux, R., Liotta, D., Simoneau, B., and Yoakim, C. J. Am. Chem. Soc. 2003, 125, 428
42. Morton, H. E. and Guindon, Y. J. Org. Chem. 1985, 50, 5379
43. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, England, 1983.
44. Deslongchamps, P., Dory, Y. L., and Li, S. Can. J. Chem. 1994, 72, 2021
45. Deslongchamps, P., Jones, P. G., Li, S., Kirby, A. J., Kuusela, S., and Ma, Y. J. Chem. Soc., Perkin Trans. 2 1997, 2621
46. Olsson, R., Rundström, P., and Frejd, T. J. Chem. Soc., Perkin Trans. 1 1998, 785
47. Olsson, R., Rundström, P., Persson, B., and Frejd, T. Carbohydr. Res. 1998, 307, 13
48. Olsson, R., Berg, U., and Frejd, T. Tetrahedron 1998, 54, 3935
49. Guindon, Y. and Anderson, P. C. Tetrahedron Lett. 1987, 28, 2485
50. Guindon, Y., Anderson, P. C., Yoakim, C., Girard, Y., Berthiaume, S., and Morton, H. E. Pure Appl. Chem. 1988, 60, 1705
51. Guindon, Y., Bernstein, M. A., and Anderson, P. C. Tetrahedron Lett. 1987, 28, 2225
52. Praly, J.-P. and Lemieux, R. U. Can. J. Chem. 1987, 65, 213
53. Angyal, S. J. Angew. Chem., Int. Ed. Engl. 1969, 8, 157
54. Angyal, S. J. Adv. Carbohydr. Chem. Biochem. 1984, 42, 15
55. Results are provided as Supporting Information.
56. Lemieux, R. U., Cromer, R., and Spohr, U. Can. J. Chem. 1988, 66, 3083
57. Gravier-Pelletier, C., Ginisty, M., and Le Merrer, Y. Tetrahedron: Asymmetry 2004, 15, 189
58. Cociorva, O. M. and Lowary, T. L. Tetrahedron 2004, 60, 1481
59. El-Badri, M. H., Willenbring, D., Tantillo, D. J., and Gervay-Hague, J. J. Org. Chem. 2007, 72, 4663
60. Pedersen, C. M., Nordstrøm, L. U., and Bols, M. J. Am. Chem. Soc. 2007, 129, 9222
61. Ko, Y.-J., Shim, S.-B., and Shin, J.-H. Org. Lett. 2009, 11, 609
62. Hubbard, A. J., Jones, A. S., and Walker, R. T. Nucleic Acids Res. 1984, 12, 6827
63. Kim, K. S., Fulse, D. B., Baek, J. Y., Lee, B.-Y., and Jeon, H. B. J. Am. Chem. Soc. 2008, 130, 8537
64. Lemieux, R. U., Hendriks, K. B., Stick, R. V., and James, K. J. Am. Chem. Soc. 1975, 97, 4056
65. Seela, F. and Winkeler, H. D. J. Org. Chem. 1982, 47, 226
66. Tann, C. H., Brodfuehrer, P. R., Brundidge, S. P., Sapino, C., Jr., and Howell, H. G. J. Org. Chem. 1985, 50, 3644
67. Crich, D. and Sharma, I. Org. Lett. 2008, 10, 4731
68. Crich, D. and Cai, W. J. Org. Chem. 1999, 64, 4926
69. Crich, D. and Sun, S. J. Am. Chem. Soc. 1997, 119, 11217
70. Crich, D. and Vinogradova, O. J. Am. Chem. Soc. 2007, 129, 11756
71. Larsen, C. H., Ridgway, B. H., Shaw, J. T., and Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208
72. Smith, D. M. and Woerpel, K. A. Org. Lett. 2004, 6, 2063
73. Shenoy, S. R., Smith, D. M., and Woerpel, K. A. J. Am. Chem. Soc. 2006, 128, 8671
74. Krumper, J. R., Salamant, W. A., and Woerpel, K. A. Org. Lett. 2008, 10, 4907
75. Correlation between selectivities and nucleophilicities were recently demonstrated in the substitution of tetrahydropyran acetals; see ref 14b.
76. The lactols along with its decomposition products were recovered intact after a prolonged reaction time of 16 h at room temperature.
77. Jencks, W. P. Acc. Chem. Res. 1980, 13, 161
78. Jencks, W. P. Chem. Soc. Rev. 1981, 10, 345
79. Sugimura, H., Muramoto, I., Nakamura, T., and Osumi, K. Chem. Lett. 1993, 22, 169
80. Lemieux, R. U. and Morgan, A. R. J. Am. Chem. Soc. 1963, 85, 1889
81. Lemieux, R. U. and Morgan, A. R. Can. J. Chem. 1965, 43, 2214
82. Altona, C. Ph.D. Thesis, University of Leiden, 1964.
83. Smith, D. M., Tran, M. B., and Woerpel, K. A. J. Am. Chem. Soc. 2003, 125, 14149
84. Alabugin, I. V. and Zeidan, T. A. J. Am. Chem. Soc. 2002, 124, 3175
85. Seeman, J. I. Chem. Rev. 1983, 83, 83
86. Seeman, J. I. J. Chem. Educ. 1986, 63, 42
87. Curtin, D. Y. Rec. Chem. Prog. 1954, 15, 111