C4′-Spiroalkylated Nucleosides Having Sulfur Incorporated at the Apex Position

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8625-8634

  Paquette, Leo A ^a   Fabris, Fabrizio ^a   Gallou, Fabrice ^a   Dong, Shuzhi ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDES;

ISOMERS; KETONES; ORGANIC ACIDS; X RAY CRYSTALLOGRAPHY;

PROTEINS;

ACETAL; KETONE DERIVATIVE; MANDELIC ACID; NUCLEOSIDE; SULFUR; ACETAL DERIVATIVE; COMPLEMENT COMPONENT C4; KETONE; MANDELIC ACID DERIVATIVE; SPIRO COMPOUND;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMER; PINACOL REARRANGEMENT; PUMMERER REACTION; X RAY CRYSTALLOGRAPHY; ALKYLATION; CHEMISTRY; ISOMERISM; SYNTHESIS;

ACETALS; ALKYLATION; COMPLEMENT C4; CRYSTALLOGRAPHY, X-RAY; ISOMERISM; KETONES; MANDELIC ACIDS; NUCLEOSIDES; SPIRO COMPOUNDS; SULFUR; THIONUCLEOSIDES;

EID: 0142258958     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030196w     Document Type: Article

References (68)

1. For example: (a) Secrist, J. A., III; Tiwari, K. N.; Riordan, J. M.; Montgomery, J. A. J. Med. Chem. 1991, 34, 2361.
2. (b) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782.
3. (c) Ewing, D. F.; Mackenzie, G. Nucleosides Nucleotides 1996, 15, 809.
4. (d) Van Draanen, N. A.; Freeman, G. A.; Short, S. A.; Harvey, R.; Jansen, R.; Szczech, G.; Koszalka, G. W. J. Med. Chem. 1996, 39, 538.
5. (e) Rahim, S. G.; Trivedi, N.; Bogunovic-Batchelor, M. V.; Hardy, G. W.; Mills, G.; Selway, J. W. T.; Snowden, W.; Littler, E.; Coe, P. L.; Basnak, I.; Whale, R. F.; Walker, R. T. J. Med. Chem. 1996, 39, 789.
6. (f) Review: Yokoyama, M. Synthesis 2000, 1637.
7. Chao, Q.; Nair, V. Tetrahedron 1997, 53, 1957 and relevant references therein.
8. (a) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Chem. Soc., Chem. Commun. 1991, 741.
9. (b) Tiwari, K. N.; Secrist, J. A., III; Montgomery, J. A. Nucleosides Nucleotides 1994, 13, 1819.
10. (c) Young, R. J.; Shaw-Ponter, S.; Thomson, J. B.; Miller, J. A.; Cumming, J. G.; Pugh, A. W.; Rider, P. Bioorg. Med. Chem. Lett. 1995, 5, 2599.
11. (a) Yoshimura, Y.; Watanabe, M.; Satoh, H.; Ashida, N.; Ijichi, K.; Sakata, S.; Machida, H.; Matsuda, A. J. Med. Chem. 1997, 40, 2177
12. (b) Satoh, H.; Yoshimura, Y.; Watanabe, M.; Ashida, N.; Ijichi, K.; Sakata, S.; Machida, H.; Matsuda, A. Nucleosides Nucleotides 1998, 17, 65.
13. (a) Nishizono, N.; Koike, N.; Yamagata, Y.; Fujii, S.; Matsuda, A. Tetrahedron Lett. 1996, 37, 7569.
14. (b) Ichikawa, E.; Yamamura, S.; Kato, K. Tetrahedron Lett. 1999, 40, 7385.
15. (a) Beach, J. W.; 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.
16. (b) 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.
17. (c) Jeong, L. S.; Schinazi, R. F.; Beach, J. W.; Kim, H. O.; Shanmuganathan, K.; Nampalli, S.; Chun, M. W.; Chung, W. K.; Choi, B. G.; Chu, C. K. J. Med. Chem. 1993, 36, 2627.
18. (d) 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.
19. (e) Brånalt, J.; Kvarnström, I.; Classon, B.; Samuelsson, B. J. Org. Chem. 1996, 61, 3604.
20. (a) Brånalt, J.; Kvarnström, I.; Classon, B.; Samuelson, B. J. Org. Chem. 1996, 61, 3611.
21. (b) Nguyen-Ba, N.; Brown, W. L.; Chan, L.; Lee, N.; Brasili, L.; Lafleur, D.; Zacharie, B. Chem. Commun. 1999, 1245.
22. (a) Chang, C.-N.; Doong, S.-L.; Zhou, J. H.; Beach, J. W.; Jeong, L. S.; Chu, C. K.; Tsai, C.-h.; Cheng, Y.-c. J. Biol. Chem. 1992, 267, 13938.
23. (b) Chang, C.-N.; Skalski, V.; Zhou, J. H.; Cheng, Y-.c. J. Biol. Chem 1992, 267, 22414.
24. (c) Coates, J. A. V.; Cammack, N.; Jenkinson, H. J.; Mutton, I. M.; Pearson, B. A.; Storer, R.; Cameron, J. M.; Penn, C. R. Antimicrob. Agents Chemother. 1992, 36, 202.
25. (d) Schinazi, R. F.; Chu, C. K.; Peck, A.; McMillan, A.; Mathis, R.; Cannon, D.; Jeong, L.-S.; Beach, J. W.; Choi, W.-B.; Yeola, S.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 672.
26. (e) Hoong, L. K.; Strange, L. E.; Liotta, D. C.; Koszalka, G. W.; Burns, C. L.; Schinazi, R. F. J. Org. Chem. 1992, 57, 5563.
27. (f) Furman, P. A.; Davis, M.; Liotta, D. C.; Paff, M.; Frick, L. W.; Nelson, D. J.; Dornsife, R. E.; Wurster, J. A.; Wilson, L. J.; Fyfe, J. A.; Tuttle, J. V.; Miller, W. H.; Condreay, L.; Averett, D. R.; Schinazi, R. F.; Painter, G. R. Antimicrob. Agents Chemother. 1992, 36, 2686.
28. (g) Mansuri, M. M.; Farina, V.; Starrett, J. E., Jr.; Benigni, D. A.; Brankovan, V.; Martin, J. C. Bioorg. Med. Chem. Lett. 1991, 1, 65.
29. (h) Lin, T.-S.; Luo, M.-Z.; Liu, M.-C.; Pai, S. B.; Dutschman, G. E.; Cheng, Y.-C. J. Med. Chem. 1994, 37, 798.
30. (i) Gosselin, G.; Schinazi, R. F.; Sommadossi, J.-P.; Mathé, C.; Bergogne, M.-C.; Aubertin, A.-M.; Kirn, A.; Imbach, J.-L. Antimicrob. Agents Chemother. 1994, 38, 1292.
31. Jung, M. E.; Kretschik, O. J. Org. Chem. 1998, 63, 2975.
32. Paquette, L. A.; Dullweber, U.; Branan, B. M. Heterocycles 1994, 37, 187.
33. Paquette, L. A.; Owen, D. R.; Bibart, R. T.; Seekamp, C. K.; Kahane, A. L.; Lanter, J. C.; Corral, M. A. J. Org. Chem. 2001, 66, 2828.
34. (a) Paquette, L. A.; Bibart, R. T.; Seekamp, C. K.; Kahane, A. L. Org. Lett. 2001, 3, 4039.
35. (b) Paquette, L. A.; Owen, D. R.; Bibart, R. T.; Seekamp, C. K. Org. Lett. 2001, 3, 4043.
36. (c) Paquette, L. A.; Seekamp, C. K.; Kahane, A. L. submitted for publication.
37. (a) Johnson, C. R. Aldrichim. Acta 1985, 18, 3.
38. (b) Johnson, C. R.; Zeller, J. R. J. Am. Chem. Soc. 1982, 104, 4021.
39. For a preliminary report of the sulfoximine results, consult: Paquette, L. A.; Lanter, J. C.; Owen, D. R.; Fabris, F.; Bibart, R. T.; Alvarez, M. Heterocycles 2001, 54, 49.
40. Dimitroff, M.; Fallis, A. G. Tetrahedron Lett. 1998, 39, 2527.
41. Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839.
42. (a) Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887.
43. (b) Madesclaire, M. Tetrahedron 1986, 42, 5459.
44. Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282.
45. (a) Gupta, D. N.; Hodge, P.; Davies, J. E. J. Chem. Soc., Perkin Trans. 1 1981, 2970.
46. (b) Bellingham, R.; Jarowicki, K.; Kocienski, P.; Martin, V. Synthesis 1996, 285.
47. For these experiments, the solid reagents were not completely dried because total dryness gave evidence of prolonging reaction times and lowering reaction efficiency. This phenomenon has been seen in other contexts: Daumas, M.; Vo-Quang, Y.; Vo-Quang, L.; LeGoffic, F. Synthesis 1989, 64.
48. De Lucchi, O.; Miotti, U.; Modena, G. Org. React. 1991, 40, 157.
49. Calinaud, P.; Gelas, J. Can. J. Chem. 1983, 61, 2103.
50. (a) O'Connor, D. E.; Broaddus, C. D. J. Am. Chem. Soc. 1964, 86, 2267.
51. (b) Kimmelma, R. Acta Chem. Scand. 1993, 47, 706.
52. (c) O'Connor, D. E.; Lyness, W. I. J. Am. Chem. Soc. 1964, 86, 3840.
53. (a) Guittet, E.; Julia, S. Synth. Commun. 1981, 11, 709.
54. (b) Crumbie, R. L.; Ridley, D. D.; Steel, P. J. Aust. J. Chem. 1985, 38, 119.
55. (c) Hoffmann, R. W.; Goldmann, S.; Maak, N.; Gerlach, R.; Frickel, F.; Steinbach, G. Chem. Ber. 1980, 113, 819.
56. Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 48, 11263.
57. Yamagiwa, S.; Sato, H.; Hoshi, N.; Kosugi, H.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1979, 570.
58. Fabris, F. Unpublished findings.
59. Houllemare, D.; Ponthieux, S.; Outurquin, F.; Paulmier, C. Synthesis 1997, 101.
60. Mozingo, R.; Harris, S. A.; Wolf, D. E.; Hoffhine, C. E., Jr.; Easton, N. R.; Folkers, K. J. Am. Chem. Soc. 1945, 67, 2092.
61. Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
62. O'Neil, I. A.; Hamilton, K. M. Synlett 1992, 791.
63. Ichikawa, E.; Yamamura, S.; Kato, K. Tetrahedron Lett. 1999, 40, 7385.
64. (a) Zou, R.; Robins, M. J. Can. J. Chem. 1987, 65, 1436.
65. (b) Robins, M. J.; Zou, R.; Hanske, F.; Madej, D.; Tyrrell, D. L. J. Nucleosides Nucleotides 1989, 8, 725.
66. (c) Robins, M. J.; Zou, R.; Guo, Z.; Wnuk, S. F.; J. Org. Chem. 1996, 61, 9207.
67. Jeong, L. S.; Kim, H. O.; Moon, H. R.; Hong, J. H.; Yoo, S. Y.; Choi, W. J.; Chun, M. W.; Lee, C. K. J. Med. Chem. 2001, 44, 806.
68. Vorbrüggen, H.; Ruh-Pohlenz, C. Org. React. 2000, 55, 1-630.