Stannyl radical-mediated cleavage of π-deficient heterocyclic sulfones. Synthesis of α-fluoro esters and the first homonucleoside α-fluoromethylene phosphonate

Journal of the American Chemical Society

Volumn 118, Issue 10, 1996, Pages 2519-2520

  Wnuk, Stanislaw F ^a   Robins, Morris J ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029975902     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953513s     Document Type: Article

References (49)

1. Nucleic Acid Related Compounds. 89. Part 88: Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902-7908.
2. Nucleic Acid Related Compounds. 89. Part 88: Robins, M. J.; Wilson, J. S.; Madej, D.; Low, N. H.; Hansske, F.; Wnuk, S. F. J. Org. Chem. 1995, 60, 7902-7908.
3. Engel, R. Chem. Rev. 1977, 77, 349-367.
4. Blackburn, G. M.; Perrée, T. D.; Rashid, A.; Bisbal, C.; Lebleu, B. Chem. Scr. 1986, 26, 21-24.
5. (a) Blackburn, G. M.; Kent, D. E.; Kolkmann, F. J. Chem. Soc., Perkin Trans, 1 1984, 1119-1125.
6. (b) Blackburn, G. M.; Guo, M.-J.; Langston, S. P.; Taylor, G. E. Tetrahedron Lett. 1990, 31, 5637-5640.
7. (c) Blackburn, G. M.; Langston, S. P. Tetrahedron Lett. 1991, 32, 6425-6428.
8. (a) Davisson, V. J.; Davis, D. R.; Dixit, V. M.; Poulter, C. D. J. Org. Chem. 1987, 52, 1794-1801.
9. (b) Hebel, D.; Kirk, K. L.; Kinjo, J.; Kovács, T.; Lesiak, K.; Baizarini, J.; De Clercq, E.; Torrence, P. F. Bioorg. Med. Chem. Lett. 1991, 1, 357-360.
10. (a) Casara, P. J.; Jund, K. C.; Clauss, A.; Navé, J.-F.; Snyder, R. D. Bioorg. Med. Chem. Lett. 1992, 2, 145-148.
11. (b) Blackburn, G. M.; Guo, M.-J. Tetrahedron Lett. 1993, 34, 149-152.
12. Jones, G. H.; Moffatt, J. G. J. Am. Chem. Soc. 1968, 90, 5337-5338.
13. 3 but no final products were reported.
14. (a) Matulic-Adamic, J.; Usman, N. Tetrahedron Lett. 1994, 35, 3227-3230.
15. (b) Matulic-Adamic, J.; Haeberli, P.; Usman, N. J. Org. Chem. 1995, 60, 2563-2569.
16. Wolff-Kugel, D.; Halzay, S. Tetrahedron Lett. 1991, 32, 6341-6344.
17. Berkowitz, D. B.; Eggen, M.-J.; Shen, Q.; Sloss, D. G. J. Org. Chem. 1993, 58, 6174-6176.
18. Halazy, S.; Ehrhard, A.; Danzin, C. J. Am. Chem. Soc. 1991, 113, 315-317.
19. Burton, D. J.; Flynn, R. M. J. Fluorine Chem. 1977, 10, 329-332.
20. Differding, E.; Duthaler, R. O.; Krieger, A.; Rüegg. G. M.; Schmit, C. Synlett 1991, 395-396.
21. Obayashi, M.; Ito, E.; Matsui, K.; Kondo, K. Tetrahedron Lett. 1982, 23, 2323-2326.
22. Yang, Z.-Y.; Burton, D. J. J. Org. Chem. 1992, 57, 4676-4683.
23. Koizumi, T.; Hagi, T.; Horie, Y; Takeuchi. Y. Chem. Pharm. Bull. 1987, 35, 3959-3962.
24. Lal, G. S. J. Org. Chem. 1993, 58, 2791-2796.
25. (a) Corey, E. J.; Samuelsson, B. J. Org. Chem. 1984, 49, 4735-4735.
26. (b) Vanna R. S.: Hogan. M. E. Tetrahedron Lett. 1992, 33, 7719-7720.
27. (a) Barton, D. H. R.; Géro, S. D.; Quiclet-Sire, B.; Samadi, M. J. Chem. Soc., Chem. Commun. 1989, 1000-1001.
28. (b) Barton, D. H. R.; Géro, S. D.; Quiclet-Sire. B.; Samadi, M. Tetrahedron 1992, 48, 1627-1636.
29. (c) Barton. D. H. R.; Géro. S. D.; Quiclet-Sire, B.; Samadi, M. J. Chem. Soc., Chem. Commun. 1988, 1372-1373.
30. 20a,b has been noted, but 2 was contaminated (5-15%) by compound(s) with similar NMR signals. A 4′(S) diastereomer should undergo parallel transformations to give parallel byproducts observed at each stage.
31. (a) Robins, M. J.; Wnuk, S. F. J. Org. Chem. 1993, 55, 3800-3801.
32. (b) Wnuk, S. F.; Robins, M. J. J. Org. Chem. 1990, 55, 4757-4760.
33. F-H = 24.9 Hz).
34. (a) Wang, Y; Jiang, Y. Synth. Commun. 1992, 22, 2287-2291.
35. (b) Thenappan, A.; Burton, D. J. J. Org. Chem. 1990, 55, 2311-2317.
36. (a) Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon Press: Oxford. 1993.
37. (b) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903-917.
38. (c) Van Dort, P. C.; Fuchs, P. L. J. Am. Chem. Soc. 1994, 116, 5657-5661.
39. (d) Jin, Z.; Vandort, P. C.; Fuchs, P. L. Phosphorus, Sulfur Silicon Relat. Elem. 1994, 95-96, 1-19.
40. (a) Neumann, W. P. Synthesis 1987, 665-683.
41. (b) Pereyre, M; Quintard, J.-P.; Rahm. A. Tin in Organic Synthesis; Butterworths: London, 1987.
42. (a) Watanabe, Y.; Ueno, Y.; Araki, T.; Endo, T.; Okawara, M. Tetrahedron Lett. 1986, 27, 215-218.
43. (b) McCarthy J. R.; Matthews D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7440.
44. (c) Wnuk, S. F.; Yuan, C-S.; Borchardt, R. T.; Balzarini, J.; De Clercq, E.; Robins, M. J. J. Med. Chem. 1994, 37, 3579-3587.
45. Antonio, Y.; De La Cruz, M. E.; Galeazzi, E.; Guzman, A.; Bray, B. L.; Greenhouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J. Chem. 1994, 72, 15-22.
46. Ueno, Y.; Aoki, S.; Okawara, M. J. Am. Chem. Soc. 1979, 101, 5414-5415.
47. Bertrand, M. P. Org. Prep. Proced. Int. 1994, 26, 257-290.
48. 23b (154 mg. 95%).
49. Rozen, S.; Filler, R. Tetrahedron 1985, 41, 1111-1153.