Mild generation of 5-(2′-deoxyuridinyl)methyl radical from a phenyl selenide precursor

Organic Letters

Volumn 6, Issue 26, 2004, Pages 5011-5013

  In, Seok Hong ^a   Greenberg, Marc M ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTATHIONE; HYDROGEN; METHYL GROUP; NUCLEIC ACID; NUCLEOSIDE; PHENYL GROUP; PHENYL SELENIDE; RADICAL; THYMIDINE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; PHOTOCHEMISTRY; PHOTOLYSIS; PRECURSOR; SYNTHESIS; TEMPERATURE;

DEOXYURIDINE; FREE RADICALS; MOLECULAR CONFORMATION; ORGANOSELENIUM COMPOUNDS; PHOTOCHEMISTRY;

EID: 12344268853     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol047754t     Document Type: Article

References (22)

1. Greenberg, M. M. Chem. Res. Toxicol. 1998, 11, 1235-1248.
2. Greenberg, M. M. In Comprehensive Natural Products Chemistry; Kool, E. T., Ed.; Elsevier: Amsterdam, 1999; Vol. 7, pp 371-426.
3. Meggers, E.; Michel-Beyerle, M. E.; Giese, B. J. Am. Chem. Soc. 1998, 120, 12950-12955.
4. Tallman, K. A.; Tronche, C.; Yoo, D. J.; Greenberg, M. M. J. Am. Chem. Soc. 1998, 120, 4903-4909.
5. Carter, K. N.; Greenberg, M. M. J. Am. Chem. Soc. 2003, 125, 13376-13378.
6. Bales, B. C.; Pitié, M.; Meunier, B.; Greenberg, M. M. J. Am. Chem. Soc. 2002, 124, 9062-9063.
7. Giese, B. Annu. Rev. Biochem. 2002, 71, 51-70.
8. Giese, B. Acc. Chem. Res. 2000, 33, 631-636.
9. Anderson, A. S.; Hwang, J. T.; Greenberg, M. M. J. Org. Chem. 2000, 65, 4648-4654.
10. Adam, W.; Arnold, M. A.; Nau, W. M.; Pischel, U.; Saha-Moeller, C. R. J. Am. Chem. Soc. 2002, 124, 3893-3904.
11. Romieu, A.; Bellon, S.; Gasparutto, D.; Cadet, J. Org. Lett. 2000, 2, 1085-1088.
12. Zhang, Q.; Wang, Y. J. Am. Chem. Soc. 2003, 125, 12795-12802.
13. Tallman, K. A.; Greenberg, M. M. J. Am. Chem. Soc. 2001, 123, 5181-5187.
14. Giese, B.; Beyrich-Graf, X.; Erdmann, P.; Giraud, L.; Imwindelried, P.; Müller, S. N.; Schwitter, U. J. Am. Chem. Soc. 1995, 117, 6146-6147.
15. Spectral density at 300 nm is less than 1% that at 350 nm. See: www.rayonet.org/spectral-graphs.html for more information.
16. Newcomb, M. Tetrahedron 1993, 49, 1151-1176.
17. Carter, K. N.; Greenberg, M. M. J. Org. Chem. 2003, 68, 4275-4280.
18. Bagiyan, G. A.; Koroleva, I. K.; Soroka, N. V.; Ufimtsev, A. V. Russ. Chem. Bull., Int. Ed. 2003, 52, 1135-1141.
19. Curran, D. P.; Martin-Esker, A., A.; Ko, S.-B.; Newcomb, M. J. Org. Chem. 1993, 58, 4691-4695.
20. Engman, L.; Andersson, C.; Morgenstern, R.; Cotgreave, I. A.; Andersson, C.-M.; Hallberg, A. Tetrahedron 1994, 50, 2929-2938.
21. Razskazovskii, Y. V.; Becker, D.; Sevilla, M. D. In S-Centered Radicals; Alfassi, Z. B., Ed.; John Wiley & Sons: Chichester, 1999.
22. Keck, G. E.; Byers, J. H. J. Org. Chem. 1985, 50, 5442-5444.