5-Exo versus 6-endo cyclization of nucleoside 2-sila-5-hexenyl radicals: Reaction of 6-(bromomethyl)dimethylsilyl 1′,2′-unsaturated uridines

Journal of Organic Chemistry

Volumn 70, Issue 5, 2005, Pages 1684-1690

  Ogamino, Junko ^a   Mizunuma, Hideaki ^a   Kumamoto, Hiroki ^a   Takeda, Shingo ^a   Haraguchi, Kazuhiro ^a   Nakamura, Kazuo T ^a   Sugiyama, Hiroshi ^b   Tanaka, Hiromichi ^a  

^a SHOWA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; OXIDATION; SILICON; SUBSTITUTION REACTIONS; SUBSTRATES; SYNTHESIS (CHEMICAL); UNSATURATED COMPOUNDS;

CYCLIZATION; CYCLIZED PRODUCTS; TAMAO OXIDATION; UNSATURATED URIDINES;

AROMATIC COMPOUNDS;

1 (BROMOMETHYL)DIMETHYLSILYL 1 [2 O BENZOYL 3,5 BIS O(TERT BUTYLDIMETHYLSILYL)DEXTRO ERYTHRO PENT 1 ENOFURANOSYL]URACIL; 6 (BROMOMETHYL)DIMETHYLSILYL 1 [3,5 BIS O(TERT BUTYLDIMETHYLSILYL) 2 C CARBOMETHOXY 2 DEOXY DEXTRO ERYTHRO PENT 1 ENOFURANOSYL]URACIL; 6 (BROMOMETHYL)DIMETHYLSILYL 1 [3,5 BIS O(TERT BUTYLDIMETHYLSILYL) 2 CHLORO 2 DEOXY DEXTRO ERYTHRO PENT 1 ENOFURANOSYL]URACIL; 6 (BROMOMETHYL)DIMETHYLSILYL 1 [3,5 BIS O(TERT BUTYLDIMETHYLSILYL) 2 DEOXY C METHYL DEXTRO ERYTHRO PENT 1 ENOFURANOSYL]URACIL; 6 (BROMOMETHYL)DIMETHYLSILYL 1 [3,5 BIS O(TERT BUTYLDIMETHYLSILYL) 2 DEOXY DEXTRO ERYTHRO PENT 1 ENOFURANOSYL]URACIL; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG; URIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; OXIDATION; STRUCTURE ACTIVITY RELATION;

CYCLIZATION; FREE RADICALS; MOLECULAR CONFORMATION; NUCLEOSIDES; ORGANOSILICON COMPOUNDS; URIDINE;

EID: 14544297394     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040260p     Document Type: Article

References (26)

1. Beckwith, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925.
2. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. Curran, D. P. Synthesis 1988, 417-439.
3. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073. Curran, D. P. Synthesis 1988, 417-439.
4. Wilt, J. W. Tetrahedron 1985, 41, 3979.
5. Nishiyama, H.; Kitajima, T.; Matsumoto, M.; Itoh, K. J. Org. Chem. 1984, 49, 2298.
6. Itoh, Y.; Haraguchi, K.; Tanaka, H.; Gen, E.; Miyasaka, T. J. Org. Chem. 1995, 60, 656.
7. Kumamoto, H.; Shindoh, S.; Tanaka, H.; Itoh, Y.; Haraguchi, K.; Gen, E.; Kittaka, A.; Miyasaka, T.; Kondo, M.; Nakamura, K. T. Tetrahedron 2000, 56, 5363.
8. Buchanan, J. G.; Wightman, R. H. In Topics in Antibiotic Chemistry; Sammes, P. G., Ed.; Ellis Horwood Ltd.: Chichester, 1982; Vol. 6, p 231.
9. For recent reports concerning the synthesis of 1′-branched nucleosides: (a) Kodama, T.; Shuto, S.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2002, 67, 7706. (b) Haraguchi, K.; Kubota, Y.; Tanaka, H. J. Org. Chem. 2004, 69, 1831.
10. For recent reports concerning the synthesis of 1′-branched nucleosides: (a) Kodama, T.; Shuto, S.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2002, 67, 7706. (b) Haraguchi, K.; Kubota, Y.; Tanaka, H. J. Org. Chem. 2004, 69, 1831.
11. Use of LHMDS in the C6-silylation of uridine derivatives has recently been reported: Yoshimura, Y.; Kumamoto, H.; Baba A.; Takeda, S.; Tanaka, H. Org. Lett. 2004, 6, 1793-1795.
12. Chatgilialoglu, C.; Woynar, H.; Ingold, K. U.; Davies, A. J. Chem. Soc., Perkin Trans. 2 1983, 555.
13. Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Tetrahedron Lett. 2000, 41, 3643.
14. Semiempirical calculations (PM3) were performed using Spartan (version 3.1) program on a SGI O2 computer.
15. For radical stabilization energies of substituents: Brocks, J. J.; Beckhaus, H.-D.; Beckwith, A. L. J.; Rüchardt, C. J. Org. Chem. 1998, 63, 1935.
16. For recent examples: (a) Della, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363. (b) Kim, K.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 67.
17. For recent examples: (a) Della, E. W.; Kostakis, C.; Smith, P. A. Org. Lett. 1999, 1, 363. (b) Kim, K.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 67.
18. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753.
19. Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95, 1253.
20. For a review: Tamao, K. In Advances in Silicon Chemistry; Larson, G. L., Ed.; JAI Press: London, 1996; Vol. 3, p 1.
21. (a) Xi, Z.; Agback, P.; Plavec, J.; Sandstrom, A.; Chattopadhyaya, J. Tetrahedron 1992, 48, 349.
22. (b) Ueno, Y.; Nagasawa, Y.; Sugimoto, I.; Kojima, N.; Kanazaki, M.; Shuto, S.; Matsuda, A. J. Org. Chem. 1998, 63, 1660.
23. (c) Kodama, T.; Shuto, S.; Nomura, M.; Matsuda, A. Chem. Eur. J. 2001, 7, 2332.
24. 3N: Fleming, I.; Henning, R.; Plaut, H. J. Chem. Soc., Chem. Commun. 1984, 29.
25. Tanaka, H.; Hayakawa, H.; Miyasaka, T. In Nucleosides and Nucleotides as Antitumor and Antiviral Agents; Chu, C. K., Baker, D. C., Eds.; Plenum Press: New York, 1993; p 23.
26. Due to a small amount of the 2′-methyl-5-exo-cyclized product (15), the oxidative cleavage of this compounds was not examined.