Synthesis of C8-adenosine adducts of arylamines using palladium catalysis

Organic Letters

Volumn 3, Issue 26, 2001, Pages 4221-4223

  Schoffers, Elke ^a   Olsen, Phil D ^a,b   Means, Jay C ^a  

^a WESTERN MICHIGAN UNIVERSITY   (United States)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE; AMINE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

ADENOSINE; AMINES; CATALYSIS; MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM;

EID: 0035961044     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016900h     Document Type: Article

References (32)

1. Garner, R. C. Mutat. Res. 1998, 402, 67-75.
2. Wang, Z.; Rizzo, C. J. Org. Lett. 2001, 3, 565-568 and references therein.
3. For cross-linked nucleosides, see: (a) Harwood, E. A.; Sigurdsson, S. T.; Edfeldt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081-5082.
4. (b) Harwood, E. A.; Hopkins, P. B.; Sigurdsson, S. T. J. Org. Chem. 2000, 65, 2959-2964.
5. (c) De Riccardis, F.; Johnson, F. Org. Lett. 2000, 2, 293-295.
6. (a) Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngassa, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779-7787.
7. (b) Wu, Y.; Ogawa, A. K.; Berger, M.; McMinn, D. L.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 7621-7632.
8. (c) Ogawa, A. K.; Wu, Y.; McMinn, D. L.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 2000, 122, 3274-3287.
9. (d) McMinn, D. L.; Ogawa, A. K.; Wu, Y.; Liu, J.; Schultz, P. G.; Romesberg, F. E. J. Am. Chem. Soc. 1999, 121, 11585-11586.
10. (a) Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem., Int. Ed. 2000, 39. 990-1009.
11. (b) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 2000, 122, 1001-1007.
12. (c) Morales, J. C.; Kool, E. T. J. Am. Chem. Soc. 1999, 121, 2323-2324.
13. (d) Chepanoske, C. L.; Langelier, C. R.; Chmiel, N. H.; David, S. S. Org. Lett. 2000, 2, 1341-1344.
14. Wood, R. D.; Mitchell, M.; Sgouros, J.; Lindahl, T. Science 2001, 291, 1284-1289.
15. Lee, B. M. Korean J. Toxicol. 1990, 6, 61-73.
16. (a) Kriek, E.; Miller, J. A.; Juhl, U.; Miller, E. C. Biochemistry 1967, 6, 177-182.
17. (b) Huang, C.-Y.; Johnson, F. Nat. Prod. Lett. 1991, 1, 3-7.
18. (c) Humphreys, W. G.; Kadlubar, F. F.; Guengerich, F. P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8278-8282.
19. Lee, M.-S.; King, C. M. Chem.-Biol. Interact. 1981, 34, 239-248.
20. Westra, J. G. Carcinogenesis 1981, 2, 355-357.
21. For highlights on aromatic heteroatom coupling reactions, see: Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615-2623.
22. De Riccardis, F.; Bonala, R. R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453-10460.
23. For recent reviews, see: (a) Hartwig, J. F. Synlett 1997, 329-340.
24. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805-818.
25. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046-2067.
26. (d) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852-860.
27. (e) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
28. Bonala, R. R.; Shishkina, I. G.; Johnson, F. Tetrahedron Lett. 2000, 41, 7281-7284.
29. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090-6091.
30. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722-9723.
31. Ogilvie, K. K.; Beaucage, S. L., Schifman, A. L., Theriault, N. Y.; Sadana, K. L. Can. J. Chem. 1978, 56, 2768-2780.
32. Hong, Y.; Tanoury, G. J.; Wilkinson, H. S.; Bakale, R. P.; Wald, S. A.; Senanayake, C. H. Tetrahedron Lett. 1997, 38, 5607-5610.