Synthesis of 8-arylsulfoxyl/sulfonyl adenines

Tetrahedron Letters

Volumn 45, Issue 52, 2004, Pages 9549-9552

  Llauger, Laura ^a   He, Huazhong ^a   Chiosis, Gabriela ^a  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

8 Arylsufonyl adenines; 8 Arylsufoxyl adenines; Alumina supported OXONE ; Oxidation

Indexed keywords

ADENINE DERIVATIVE; ALUMINUM; AMINE; PHOSPHORANE DERIVATIVE; SULFONE DERIVATIVE; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; DEPROTECTION REACTION; METHODOLOGY; MITSUNOBU REACTION; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 9644299719     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.11.009     Document Type: Article

References (28)

1. C.E. Arris, F.T. Boyle, A.H. Calvert, N.J. Curtin, J.A. Endicott, E.F. Garman, A.E. Gibson, B.T. Golding, S. Grant, R.J. Griffin, P. Jewsbury, L.N. Johnson, A.M. Lawrie, D.R. Newell, M.E. Noble, E.A. Sausville, R. Schultz, and W. Yu J. Med. Chem. 43 2000 2797 2804
2. E. Chapman, S. Ding, P.G. Schultz, and C.H. Wong J. Am. Chem. Soc. 124 2002 14524 14525
3. O.D. Perez, Y.T. Chang, G. Rosania, D. Sutherlin, and P.G. Schultz Chem. Biol. 4 2002 475 483
4. G. Chiosis, B. Lucas, H. Huezo, D. Solit, A. Basso, and N. Rosen Curr. Cancer Drug Targets 5 2003 371 376
5. R.C. Young, M. Jones, K.J. Milliner, K.K. Rana, and J.G. Ward J. Med. Chem. 33 1990 2073 2080
6. N.C. Gonnella, H. Nakanishi, J.B. Holtwick, D.S. Horowitz, and K. Kanamori J. Am. Chem. Soc. 105 1983 2050 2053
7. M. Draminsky, and E. Frass Pol. J. Chem. 61 1987 901 904
8. G. Chiosis, B. Lucas, A. Shtil, H. Huezo, and N. Rosen Bioorg. Med. Chem. 11 2002 3555 3564
9. E. Camaioni, S. Vittori, R. Volpini, K.-N. Klotz, and G. Cristalli Bioorg. Med. Chem. 6 1998 523 533
10. K-N. Klotz, S. Kachler, C. Lambertucci, S. Vittori, R. Volpini, and G. Cristalli Naunyn-Scmiedeberg's Arch. Pharmacol. 367 2003 629 634
11. H. He, L. Llauger, N. Rosen, and G. Chiosis J. Org. Chem. 69 2004 3230 3232
12. Kasibhatla, S. R.; Hong, K.; Zhang, L.; Biamonte, M. A.; Boehm, M. F.; Shi, J.; Fan, J. PCT Int. Appl., 2003, WO 2003037860
13. K. Sato, M. Hyodo, M. Aoki, X.-Q. Zheng, and R. Noyori Tetrahedron 57 2001 2469 2476
14. R.S. Varma, and K.P. Naicker Org. Lett. 2 1999 189 191
15. S. Choi, J.D. Yang, M. Ji, H. Choi, M. Kee, K.-H. Ahn, S.-H. Byeon, W. Baik, and S. Koo J. Org. Chem. 66 2002 8192 8198
16. K.C. Nicolaou, R.L. Magolda, W.J. Sipio, W.E. Barnette, Z. Lysenko, and M.M. Joullie J. Am. Chem. Soc. 102 1980 3784 3793
17. R.P. Greenhalgh Synlett 1992 235 236
18. P. Ceccherelli, M. Curini, M.C. Marcotullio, F. Epifano, and O. Rosati Synlett 1996 767 768
19. P.J. Kropp, G.W. Breton, J.D. Fields, J.C. Tung, and B.R. Loomis J. Am. Chem. Soc. 122 2000 4280 4285
20. C.J. Foti, J.D. Fields, and P.J. Kropp Org. Lett. 6 1999 903 904
21. 4, respectively
22. T.-C. Chien, C.-S. Chen, J.-Y. Yeh, K.-C. Wang, and J.-W. Chern Tetrahedron Lett. 36 1995 7881 7884
23. 3-hexanes-EtOAc at 2:2:1 to provide 1a (360 mg, 70% isolated yield)
24. B. Lucas, N. Rosen, and G. Chiosis J. Comb. Chem. 3 2001 518 520
25. 3): δ 160.5, 159.9, 152.1, 151.5, 142.3, 134.6, 133.2, 131.7, 129.9, 129.2, 128.3, 121.4, 114.6, 112.8, 55.2, 43.4, 31.5, 19.8, 13.5. MS (EIS) m/z 590.2 (M+1)
26. 3): δ 159.9, 154.2, 151, 144.6, 140.8, 133.3, 132.1, 130.2, 128.9, 128.4, 127.9, 120.9, 120.7, 112.9, 55.8, 44.5, 32.4, 20.0, 13.6. MS (EIS) m/z 622.3 (M+1)
27. 3): δ 160.6, 156.0, 154.2, 151.6, 150.1, 142.3, 130.6, 119.3, 117.7, 116.8, 109.5, 55.6, 43.8, 31.6, 19.9, 13.5. MS (EIS) m/z 346.2 (M+1)
28. 3): δ 160.1, 156.9, 155.2, 151.0, 146.1, 139.9, 130.5, 121.0, 120.5, 118.9, 112.9, 55.7, 44.8, 32.3, 19.9, 13.5. MS (EIS) m/z 362.2 (M+1)