1,5-Translocation strategy for nucleoside anomeric radicals

Nucleosides and Nucleotides

Volumn 16, Issue 7-9, 1997, Pages 1423-1426

  Kittaka, Atsushi ^a   Tanaka, Hiromichi ^a   Yamada, Naoki ^a   Kato, Hajime ^a   Miyasaka, Tadashi ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 CHLOROPURINE; NUCLEOSIDE; UNCLASSIFIED DRUG; URACIL DERIVATIVE; URIDINE DERIVATIVE;

BINDING AFFINITY; CONFERENCE PAPER; CYCLIZATION; DIAGNOSTIC APPROACH ROUTE; NUCLEOSIDE TRANSPORT; NUCLEOTIDE SEQUENCE; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0030732580     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319708006197     Document Type: Conference Paper

References (19)

1. (a) Giese, B.; Dupuis, J. Angew. Chem., Int. Ed. Engle. 1983, 22, 622-623.
2. (b) Giese, B.; Dupuis, J. Tetrahedron Lett. 1984, 25, 1349-1352.
3. Kahne, D.; Yang, D.; Lim, J. J.; Miller, R.; Paguaga, E. J. Am. Chem. Soc. 1988, 110, 8716-8717.
4. (a) Haraguchi, K.; Matsumoto, K.; Itoh, Y.; Tanaka, H.; Miyasaka, T. Nucleic Acids Symposium Series 1994, 31, 29-30.
5. (b) Itoh, Y.; Haraguchi, K.; Tanaka, H.; Matsumoto, K.; Nakamura, K. T.; Miyasaka, T. Tetrahedron Lett. 1995, 36, 3867-3870.
6. 3SiH, see: Gimisis, T.; Ialongo, G.; Zamboni, M.; Chatgilialoglu, C. Tetrahedron Lett. 1995, 36, 6781-6784.
7. Curran, D. P.; Shen, W. J. Am. Chem. Soc. 1993, 113, 6051-6059.
8. For a recent example of radical 5-endo-trig cyclization: Bogen, S.; Malacria, M. J. Am. Chem. Soc. 1996, 118, 3992-3993 and references cited therein.
9. (a) Kittaka, A.; Tanaka, H.; Yamada, N.; Miyasaka, T. Tetrahedron Lett. 1996, 37, 2801-2804.
10. (b) Almost at the same time, Gimisis and Chatgilialoglu reported the spiro nucleoside formation from compound 4, see: Gimisis, T.; Chatgilialoglu, C. J. Org. Chem. 1996, 61, 1908-1909.
11. (a) Tanaka, H.; Hayakawa, H.; Miyasaka, T. Tetrahedron 1982, 38, 2635-2642.
12. (b) Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. Chem. Pharm. Bull. 1983, 31, 787-790.
13. (c) Shimizu, M.; Tanaka, H.; Hayakawa, H.; Miyasaka, T. Tetrahedron Lett. 1990, 31, 1295-1298.
14. (a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641.
15. αe are 5.53 and 5.23 ppm, respectively.
16. Some of these compounds were also isolated by the HPLC separation in 24% combined yield (data not shown).
17. (a) Dudycz, L.; Stolarski, R.; Pless, R.; Shugar, D. J. Z. Naturforsch. 1979, 34C, 359-373.
18. (b) Evans, F. E.; Kaplan, N. O. J. Biol. Chem. 1976, 257, 6791-6797.
19. Yamazaki, N.; Eichenberger, E.; Curran, D. P. Tetrahedron Lett. 1994, 35, 6623-6626.