Synthesis of [4,5-bis(hydroxymethyl)-1,3-oxathiolan-2-yl]nucleosides as potential inhibitors of HIV via stereospecific base-induced rearrangement of a 2,3-epoxy thioacetate

Journal of Organic Chemistry

Volumn 61, Issue 11, 1996, Pages 3604-3610

  Brånalt, Jonas ^a   Kvarnström, Ingemar ^a   Classon, Björn ^b   Samuelsson, Bertil ^b,c  

^a LINKÖPING UNIVERSITY   (Sweden)

^b STOCKHOLM UNIVERSITY   (Sweden)

^c ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 OXATHIOLANE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIVIRUS AGENT; NUCLEOSIDE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030012725     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960009c     Document Type: Article

References (49)

1. For part 1 in this series, see ref 9.
2. Belleau, B.; Dixit, D. M.; Nguyen-Ba, N.; Kraus, J. L. Abstracts of Papers, Fifth International Conference on AIDS, Montreal, Canada, 1989, Abstract T.C.O.1.
3. (a) Jeong, L. S.; Schinazi, R. F.; Beach, J. W.; Kim, H. O.; Nampalli, S.; Shanmuganathan, K.; Alves, A. J.; McMillan, A.; Chu, C. K.; Mathis, R. J. Med. Chem. 1993, 36, 181.
4. (b) Jeong, L. S.; Schinazi, R. F.; Beach, J. W.; Kim, H. O.; Shanmuganathan, K.; Nampalli, S.; Chun, W.-K.; Choi, B. G.; Chu, C. K. J. Med. Chem. 1993, 36, 2627.
5. (c) Warren Beach. J.; Jeong, L. S.; Alves, A. J.; Pohl, D.; Kim, H. O.; Chang, C.-N.; Doong, S.-L.; Schinazi, R. F.; Cheng, Y.-C.; Chu, C. K. J. Org. Chem. 1992, 57, 2217.
6. Jin, H.; Siddiqui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S.; Goodyear, M. D.; Ravenscroft, P.; Beels, C. D. J. Org. Chem. 1995, 60, 2621 and references cited therein.
7. Frick, L. W.; St. John, L.; Taylor, L. C.; Painter, G. R.; Furman, P. A.; Liotta, D. C.; Furfine, E. S.; Nelson, D. J. Antimicrob. Agents Chemother. 1993, 37, 2285.
8. (a) Mansour, T. S.; Jin, H.; Wang, W.; Hooker, E. U.; Ashman, C.; Cammack, N.; Salomon, H.; Belmonte, A. R.; Wainberg, M. A. J. Med. Chem. 1995, 38, 1.
9. (b) Wang, W.; Jin, H.; Mansour, T. S. Tetrahedron Lett. 1994, 35, 4739.
10. (c) Belleau, B.; Brasili, L.; Chan, L.; DiMarco, M. P.; Zacharie, B.; Nguyen-Ba, N.; Jenkinson, H. J.; Coates, J. A. V.; Cameron, J. M. Bioorganic Med. Chem. Lett. 1993, 3, 1723.
11. (a) Brånalt, J.; Kvarnström, I.; Niklasson, G.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 1783.
12. (b) Brånalt, J.; Kvarnström, I.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 4430.
13. (c) Jansson, M.; Svansson, L.; Svensson, S. C. T.; Kvarnström, I.; Classon, B.; Samuelsson, B. Nucleosides Nucleotides 1992, 11, 1793.
14. (d) Rosenquist, A.; Kvarnström, I.; Svensson, S. C. T.; Classon, B.; Samuelsson, B. J. Org. Chem. 1994, 59, 1779.
15. (a) Svansson, L.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1991, 56, 2993.
16. (b) Sterzycki, R. Z.; Martin, J. C.; Wittman, M.; Brankovan, V.; Yang, H.; Hitchcock, M. J.; Mansuri, M. M. Nucleosides Nucleotides 1991, 10, 291.
17. (c) Bamford, M. J.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1990, 33, 2494.
18. (d) Tseng, C. K.-H.; Marquez, V. E.; Milne, G. W. A.; Wysocki, R. J.; Mitsuya, H.; Shirasaki, T.; Driscoll, J. S. J. Med. Chem. 1991, 34, 343.
19. (e) Mann, J.; Weymouth-Wilsson, A. C. J. Chem. Soc., Perkin Trans. 1 1994, 3141.
20. Brånalt, J.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 3599-3603.
21. For a racemic synthesis of 1,4-di-O-benzyl-2-thiothreitol and 1,4-di-O-benzyl-2-thioerythritol, see: Forster, R. C.; Owen, L. N. J. Chem. Soc., Perkin Trans. 1 1978, 822.
22. For a review, see: Horton, D.; Hutson, D. H. Adv. Carbohyd. Chem. 1963, 18, 123.
23. Katsuki, T.; Sharpless, K. B. J. Am. Chem. Soc. 1980, 102, 5976.
24. Behrens C. H.; Sharpless, K. B. J. Org. Chem. 1985, 50, 5696.
25. Caron, M.; Sharpless, K. B. J. Org. Chem. 1985, 50, 1560.
26. (a) Raifeld, Y. E.; Nikitenko, A. A.; Arshava, B. M. Tetrahedron: Asymmetry 1991, 2, 1083.
27. (b) Raifeld, Y. E.; Nikitenko, A. A.; Arshava, B. M.; Mikerin, I. E.; Zilberg, L. L.; Vid, G. Y.; Lang, S. A.; Lee, V. J. Tetrahedron 1994, 50, 8603.
28. (a) Uenishi, J.; Motoyama, M.; Nishiyama, Y.; Wakabayashi, S. J. Chem. Soc., Chem. Commun. 1991, 1421.
29. (b) Uenishi, J.; Motoyama, M.; Takahashi, K. Tetrahedron: Asymmetry 1994, 5, 101.
30. Gill, D. M.; Pegg, N. A.; Rayner, C. M. J. Chem. Soc., Perkin Trans. 1 1993, 1371.
31. Ko, S. Y. J. Org. Chem. 1995, 60, 6250.
32. Recently, a method for converting 2,3-epoxy amines into 3-hydroxy-1,2-aziridines was reported utilizing an aza-Payne type rearrangement: (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fujii, N.; Nimura, N.; Miwa, Y.; Taga, T.; Chounan, Y.; Yamamoto, Y. J. Org. Chem. 1995, 60, 2044. (b) Nakai, K.; Ibuka, T.; Otaka, A.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 6247.
33. Recently, a method for converting 2,3-epoxy amines into 3-hydroxy-1,2-aziridines was reported utilizing an aza-Payne type rearrangement: (a) Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fujii, N.; Nimura, N.; Miwa, Y.; Taga, T.; Chounan, Y.; Yamamoto, Y. J. Org. Chem. 1995, 60, 2044. (b) Nakai, K.; Ibuka, T.; Otaka, A.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 6247.
34. Payne, G. B. J. Org. Chem. 1962, 27, 3819.
35. Chong, J. M.; Wong, S. J. Org. Chem. 1987, 52, 2596.
36. Mitsunobu, O. Synthesis 1981, 1.
37. Volante, R. P. Tetrahedron Lett. 1981, 22, 3119.
38. See, for example: Hall, L. D.; Hough, L.; Pritchard, R. A. J. Chem. Soc. 1961, 1537.
39. For a recent report on silica gel promoted reactions, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, W. F., Jr.; Jones, J. E., III; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146. For a report on the rearrangement of oxiranes into aldehydes using silica gel, see: Lemini, C.; Ordonez M.; Perez-Flores, J.; Cruz-Almanza, R. Synth. Commun. 1995, 25, 2695.
40. For a recent report on silica gel promoted reactions, see: Kropp, P. J.; Breton, G. W.; Craig, S. L.; Crawford, S. D.; Durland, W. F., Jr.; Jones, J. E., III; Raleigh, J. S. J. Org. Chem. 1995, 60, 4146. For a report on the rearrangement of oxiranes into aldehydes using silica gel, see: Lemini, C.; Ordonez M.; Perez-Flores, J.; Cruz-Almanza, R. Synth. Commun. 1995, 25, 2695.
41. For a review on heterocyclic cations, see: Pittman, C. U.; McManus, S. P.; Larsen, J. W. Chem. Rev. 1972, 72, 357.
42. Fokin, A. V.; Kolomiets, A. F. Russ. Chem. Rev. 1975, 44, 306 and references cited therein.
43. Culvenor, C. C. J.; Davies, W.; Pausacker, K. H. J. Chem. Soc. 1946, 1050.
44. Goodman, L.; Benitez, A.; Baker, B. R. J. Am. Chem. Soc. 1958, 80, 1537.
45. 1H NOE difference spectroscopy. In both 26 and 27, H-4 and H-5 were easily distinguished by a large difference in chemical shift (0.6-0.7 ppm). Because of the higher electronegativity of oxygen compared to sulfur, it is assumed that H-5 appears at a higher chemical shift than H-4. Irradiation of H-5 in 26 gave enhancement of H-2 (1.3%) whereas irradiation of H-5 in 27 gave enhancement of the methoxy group (1.5%).
46. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
47. For the acid-catalyzed formation of dimers from 2-methoxy-1,3-oxathiolane, see: Tanimoto, S.; Miyake, T.; Okano, M. Bull. Inst. Chem. Res., Kyoto Univ. 1977, 55, 276.
48. Vial, J. M.; Johansson, N. G.; Wrang, L. Chattopadhyaya, J. Antiviral Chem. Chemother. 1990, 1, 183.
49. See, for example: Okabe, M.; Sun, R.-C.; Tam, S. Y.-K.; Todaro, L. J.; Coffen, D. L. J. Org. Chem. 1988, 53, 4780.