A New Entry to 2-Substituted Purine Nucleosides Based on Lithiation-Mediated Stannyl Transfer of 6-Chloropurine Nucleosides

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 3833-3841

  Kato, Keisuke ^a,c   Hayakawa, Hiroyuki ^a,d   Tanaka, Hiromichi ^a   Kumamoto, Hiroki ^a   Shindoh, Satoru ^a   Shuto, Satoshi ^b   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

^b HOKKAIDO UNIVERSITY   (Japan)

^c TOHO UNIVERSITY   (Japan)

^d Tsumura Laboratory   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542602181     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (35)

1. Barton, D. H. R.; Hedgecock, C. J. R.; Lederer, E.; Motherwell, W. B. Tetrahedron Lett. 1979, 279.
2. The halogen-lithium exchange of trimethylsilylated 8-bromopurine nucleosides has also been reported: Công-Danh, N.; Beaucourt, J.-P.; Pichat, L. Tetrahedron Lett. 1979, 2385.
3. Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787.
4. There can be seen an inconsistency between our result and the following report, in which 6-chloro-9-(tetrahydropyran-2-yl)purine underwent 8-lithiation with butyllithium and, upon treatment with carbon electrophiles, gave the 8-carbon-substituted derivatives in good yields: Leonard, N. J.; Bryant, J. D. J. Org. Chem. 1979, 44, 4612.
5. For the LDA lithiation of naturally occurring purine nucleosides, see: (a) Hayakawa, H.; Haraguchi, K.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 72.
6. (b) Hayakawa, H.; Tanaka, H.; Haraguchi, K.; Mayumi, M.; Nakajima, M.; Sakamaki, T.; Miyasaka, T. Nucleosides Nucleotides 1988, 7, 121. Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189.
7. (b) Hayakawa, H.; Tanaka, H.; Haraguchi, K.; Mayumi, M.; Nakajima, M.; Sakamaki, T.; Miyasaka, T. Nucleosides Nucleotides 1988, 7, 121. Hayakawa, H.; Tanaka, H.; Sasaki, K.; Haraguchi, K.; Saitoh, T.; Takai, F.; Miyasaka, T. J. Heterocycl. Chem. 1989, 26, 189.
8. Saenger, W. Principles of Nucleic Acid Structure; Springer-Verlag: New York, 1984.
9. For a review article, see: Srivastava, P. C.; Robins, R. K.; Meyer, R. B., Jr. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1988; Vol. 1, pp 113-281.
10. Maeda, M.; Nushi, K.; Kawazoe, Y. Tetrahedron 1974, 30, 2677.
11. Matsuda, A.; Nomoto, Y.; Ueda, T. Chem. Pharm. Bull. 1979, 27, 183.
12. (a) Nair, V.; Lyons, A. G. Tetrahedron 1990, 46, 7677.
13. (b) Nair, V.; Purdy, D. F. Tetrahedron 1991, 47, 365.
14. (c) Adah, S. A.; Nair, V. Tetrahedron Lett. 1995, 36, 6371.
15. (a) Matsuda, A.; Shonozaki, M.; Miyasaka, T.; Machida, H.; Abiru, T. Chem. Pharm. Bull. 1985, 33, 1766.
16. (b) Matsuda, A.; Shinozaki, M.; Yamaguchi, T.; Homma, H.; Nomoto, R.; Miyasaka, T.; Watanabe, Y.; Abiru, T. J. Med. Chem. 1992, 35, 241.
17. (a) Nair, V.; Richardson, S. G. Synthesis 1982, 670.
18. (b) Nair, V.; Young, D. A. J. Org. Chem. 1985, 50, 406.
19. A preliminary communication of the present study has been reported: Kato, K.; Hayakawa, H.; Tanaka, H.; Kumamoto, H.; Miyasaka, T. Tetrahedron Lett. 1995, 36, 6507.
20. Protonolysis of stannylated heterocycles with silica gel has been reported: Sakamoto, T.; Uchiyama, D.; Kondo, Y.; Yamanaka, H. Chem. Pharm. Bull. 1993, 41, 478.
21. For an example of anionic C-C silyl rearrangement, see: Daney, M.; Lapouyade, R.; Bouas-Laurent, H. J. Org. Chem. 1983, 48, 5055.
22. Rearrangement of a stannyl group has been reported recently in the lithiation of a stannylated heterocycle: Kelly, T. R.; Lang, F. Tetrahedron Lett. 1995, 36, 9293.
23. Although almost quantitative formation of the 8-tributylstannyl derivative was apparent from TLC analysis (basic alumina plate, hexane/EtOAc = 10/1) of the reaction mixture, the product was isolated only in 35% yield after Florisil column chromatography, resulting in the formation of the starting material in 50% yield (see the Experimental Section).
24. For a review concerning the Stille reaction, see: Mitchell, T. N. Synthesis 1992, 803.
25. It has been reported that the extent of lithiation at the 6-position of uridine (or acyclouridine) derivatives is affected by the structure of the sugar (or acyclic) moiety: (a) Hayakawa, H.; Tanaka, H.; Maruyama, Y.; Miyasaka, T. Chem. Lett. 1985, 1401. (b) Hayakawa, H.; Tanaka, H.; Obi, K.; Itoh, M.; Miyasaka, T. Tetrahedron Lett. 1987, 28, 87. Tanaka, H.; Miyasaka, T.; Sekiya, K.; Takashima, H.; Ubasawa, M.; Nitta, I.; Baba, M.; Walker, R. T.; De Clercq, E. Nucleosides Nucleotides 1992, 11, 447.
26. It has been reported that the extent of lithiation at the 6-position of uridine (or acyclouridine) derivatives is affected by the structure of the sugar (or acyclic) moiety: (a) Hayakawa, H.; Tanaka, H.; Maruyama, Y.; Miyasaka, T. Chem. Lett. 1985, 1401. (b) Hayakawa, H.; Tanaka, H.; Obi, K.; Itoh, M.; Miyasaka, T. Tetrahedron Lett. 1987, 28, 87. Tanaka, H.; Miyasaka, T.; Sekiya, K.; Takashima, H.; Ubasawa, M.; Nitta, I.; Baba, M.; Walker, R. T.; De Clercq, E. Nucleosides Nucleotides 1992, 11, 447.
27. It has been reported that the extent of lithiation at the 6-position of uridine (or acyclouridine) derivatives is affected by the structure of the sugar (or acyclic) moiety: (a) Hayakawa, H.; Tanaka, H.; Maruyama, Y.; Miyasaka, T. Chem. Lett. 1985, 1401. (b) Hayakawa, H.; Tanaka, H.; Obi, K.; Itoh, M.; Miyasaka, T. Tetrahedron Lett. 1987, 28, 87. Tanaka, H.; Miyasaka, T.; Sekiya, K.; Takashima, H.; Ubasawa, M.; Nitta, I.; Baba, M.; Walker, R. T.; De Clercq, E. Nucleosides Nucleotides 1992, 11, 447.
28. (a) Tius, M. A.; Kawakami, J. K. Synth. Commun. 1992, 22, 1461.
29. (b) Tius, M. A. Tetrahedron 1995, 51, 6605.
30. Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003.
31. Yamamoto, Y.; Yanagi, A. Chem. Pharm. Bull. 1982, 30, 2003.
32. Destannylation with aqueous ammonia has been reported in the reaction of a stannylated heterocycle: Uchiyama, D.; Yabe, M.; Kameyama, H.; Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1996, 43, 1301.
33. For a review article concerning nucleoside antibiotics, see: Isono, K. J. Antibiot. 1988, 41, 1711.
34. For a recent example, see: Obara, T.; Shuto, S.; Saito, Y.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Matsuda, A. J. Med. Chem. 1996, 39, 3847.
35. Shuto, S.; Obara, T.; Toriya, M.; Hosoya, M.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 324.