A one-pot method for the stereoselective introduction of a vinyl group via an atom-transfer radical-cyclization reaction with a diphenylvinylsilyl group as a temporary connecting tether. Synthesis of 4'α-C-vinylthymidine, a potent antiviral nucleoside

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 7153-7157

  Sugimoto, Isamu ^a   Shuto, Satoshi ^a   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4'ALPHA C VINYLTHYMIDINE; ALKANOL; ANTIVIRUS AGENT; DIPHENYLVINYLSILYL DERIVATIVE; HYDROXYL GROUP; INDAN DERIVATIVE; ORGANOHALOGEN DERIVATIVE; THYMIDINE DERIVATIVE; TRIBUTYLTIN; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033578697     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990787f     Document Type: Article

References (58)

1. Nucleosides and Nucleotides. 188. Part 187: Fukuoka, M.; Shuto, S.; Minakawa, N.; Ueno, Y.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5361-5364.
2. (a) Giese, B.; Kopping, B.; Gobel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301-856.
3. (b) Curran, D. P.; Porter, N. A.; Giese, B. Stereochemistry of radical reactions; VCH: Weinheim, 1996.
4. (c) Motherwell, W. B.; Crich, D. Free-Radical Chain Reactions in Organic Synthesis; Academic Press: London, 1992.
5. (d) Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 4, pp 715-831.
6. (e) Jasperse, C. P.; Curran, D. P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
7. (f) Thebtaranonth, C.; Thebtaranonth, Y. Tetrahedron 1990, 46, 1385-1489.
8. (f) Laird, E. E.; Jorgensen, W. L. J. Org. Chem. 1990, 55, 9-27.
9. (a) Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298-2300.
10. (b) Stork, G.; Kahn, M. J. Am. Chem. Soc. 1985, 107, 500-501.
11. (c) Magnol, E.; Malacria, M. Tetrahedron Lett. 1986, 27, 2255-2256.
12. (d) Koreeda, M.; George, I. A. J. Am. Chem. Soc. 1986, 108, 8098-8100.
13. (e) Tamao, K.; Maeda, K.; Yamaguchi, T.; Ito, Y. J. Am. Chem. Soc. 1989, 111, 4984-4985.
14. (f) Walkup, R. D.; Kane, R. R.; Obeyesekere, N. U. Tetrahedron Lett. 1990, 31, 1531-1534.
15. (g) Koreeda, M.; Hamann, L. G. J. Am. Chem. Soc. 1990, 112, 8175-8177.
16. (h) Myers, A. G.; Gin, D. Y.; Widdowson, K. L. J. Am. Chem. Soc. 1991, 113, 9661-9663.
17. (i) Hutchinson, J. H.; Daynard, T. S.; Gillard, J. W. Tetrahedron Lett. 1991, 32, 573-576.
18. (j) Koot, W.-J.; van Ginkel, R.; Kranenburg, M.; Hiemstra, H.; Louwrier, S.; Moolenaar, M. J.; Speckamp, W. N. Tetrahedron Lett. 1991, 32, 401-404.
19. (k) Stork, G.; Suh, H. S. Kim. G. J. Am. Chem. Soc. 1991, 113, 7054-7056.
20. (l) Xi, A.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. B. Tetrahedron 1992, 58 349-370.
21. (m) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332-8333.
22. (n) Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253-1277.
23. (o) Fensterbark, L.; Malacria, M.; Sieburth, S. M. Synthesis 1997, 813-854.
24. Curran, D. P.; Chang, C. J. Org. Chem. 1986, 54, 3140-3157.
25. Atom-transfer radical-cyclization reactions: (a) Chow, Y. L.; Perry, R. A. Can. J. Chem. 1985, 63, 2203-2210.
26. (b) Loye, H. C.; Faltens, T. A.; Stacy, A. M. J. Am. Chem. Soc. 1986, 108, 2488-2489.
27. (c) Bernardi, A.; Cardani, S.; Poil, G.; Scolastico, C. J. Org. Chem. 1986, 51, 5043-5045.
28. (d) Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477-2480.
29. (e) Haaima, G.; Weavers, T. Tetrahedron Lett. 1988, 29, 1085-1088.
30. (f) Lee, G. M.; Parvez, M.; Weinreb, S. M. Tetrahedron 1988, 44, 4671-4678.
31. (g) Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826-1831.
32. (h) Curran, D. P.; Shen, W.; Zhang, J.; Heffner, T. A. J. Am. Chem. Soc. 1990, 112, 6738-6740.
33. (i) Byers, J. H.; Gleason, T. G.; Knight, K. S. J. Chem. Soc., Chem. Commun. 1991, 354-356.
34. (j) Curran, D. P.; Tamine, J. J. Org. Chem. 1991, 56, 2746-2750.
35. (k) Belvisi, L.; Gennari, C.; Poli, G.; Scolastico, C.; Salom, B.; Vassalo, M. Tetrahedron 1992, 48, 3945-3960.
36. (l) Curran, D. P.; Geib, S. J.; Lin, C. H. Tetrahedron: Asymmetry 1994, 5, 199-202.
37. (m) Martinez-Grau, A.; Curran, D. P.; J. Org. Chem. 1996, 60, 8332-8333.
38. Ichikawa, S.; Shuto, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1997, 61, 1368-1375 and references therein.
39. (a) Matsuda, A.; Nakajima, Y.; Azuma, A.; Tanaka, M.; Sasaki, T. J. Med. Chem. 1991, 34, 2917-2919.
40. (b) Azuma, A.; Nakajima, Y.; Nishizono, N.; Minakawa, N.; Suzuki, M.; Hanaoka, K.; Kobayashi, T.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1993, 36, 4183-4189.
41. (c) Tanaka, M.; Matsuda, A.; Terao, T.; Sasaki, T. Cancer Lett. 1992, 64, 67-74.
42. (d) Azuma, A.; Hanaoka, K.; Kurihara, A.; Kobayashi, T.; Miyauchi, S.; Kamo, N.; Tanaka, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1995, 38, 3391-3397.
43. (a) Matsuda, A.; Hattori, H.; Tanaka, M.; Sasaki, T. Bioorg. Med. Chem. Lett. 1996, 6, 1887-1892.
44. (b) Tabata, S.; Tanaka, M.; Matsuda, A.; Fukushima, M.; Sasaki, T. Oncol. Rep. 1996, 3, 1029-1034.
45. (c) Hattori, H.; Tanaka, M.; Fukushima, M.; Sasaki, T.; Matsuda, A. J. Med. Chem. 1996, 39, 5005-5011.
46. Sugimoto, I.; Shuto, S.; Mori, S.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. Lett. 1999, 9, 385-388. Compound 1 was synthesized as below from known thymidine derivative 13 in 26% overall yield by 10-step reactions. equation presented
47. (a) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 1997, 62, 5676-5677.
48. (b) Shuto, S.; Kanazaki, M.; Ichikawa, S.; Minakawa, N.; Matsuda, A. J. Org. Chem. 1998, 63, 746-754.
49. (c) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660-1667.
50. (e) Yahiro, Y.; Ichikawa, S.; Shuto, S.; Matsuda, A. Tetrahedron Lett. 1999, 40, 5527-5531.
51. Tamao, K.; Ishida, N.; Kumada, M. J. Org. Chem. 1983, 48, 2122-2124.
52. 1H NMR analysis with 5.
53. A small coupling constant between H-1 and 2 (J < 2.2 Hz) indicated the 1,2-cis stereochemistry of 9.
54. Giese, B.; Erdmann, P.; Schafer, T.; Schwitter, U. Synthesis 1994, 1310-3112.
55. Moufid, N.; Renaud, P. Helv. Chim. Acta 1995,78,1001-1005.
56. Torii, S.; Ueyama, K.; Ono M. Tetrahedron Lett. 1980, 21, 2741-2744.
57. Barluenga, J.; Rodriguez, M. A.; Campos, P. J. J. Chem. Soc., Perkin Trans. 1 1990, 2807-2809.
58. Palumbo, G.; Ferreri, C.; Caputo, R. Tetrahedron Lett. 1983, 24, 1307-1310.