Chiral syntheses of 6′-β-fluoroaristeromycin, 6′-β-fluoro-5′-noraristeromycin and aristeromycin

Tetrahedron Letters

Volumn 46, Issue 44, 2005, Pages 7535-7538

  Yin, Xue Qiang ^a   Schneller, Stewart W ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

Carbocylic nucleosides; Epoxide ring opening; Pentasubstituted cyclopentanes

Indexed keywords

6' BETA FLUORO 5' NORARISTEROMYCIN; 6' BETA FLUOROARISTEROMYCIN; ANTIBIOTIC AGENT; ARISTEROMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 26244461975     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.163     Document Type: Article

References (34)

1. S.W. Schneller Curr. Top. Med. Chem. 2 2002 1087 1092
2. J.B. Rodriguez, and M.J. Comin Mini Rev. Med. Chem. 3 2003 95 114
3. A.B. Cheikh, L.E. Craine, S.G. Recher, and J. Zemlicka J. Org. Chem. 53 1988 929 936
4. G.V.B. Madhavan, D.P.C. McGee, R.M. Rydzewski, R. Boehme, J.C. Martin, and E.J. Prisbe J. Med. Chem. 31 1988 1798 1804
5. J.H. Hong, C.H. Oh, and J.H. Cho Tetrahedron 59 2003 6103 6108
6. J.W. Kim, B.G. Choi, and J.H. Hong Bull. Korean Chem. Soc. 25 2004 1812 1816
7. E. Ruediger, A. Martel, N. Meanwell, C. Solomon, and B. Turmel Tetrahedron Lett. 45 2004 739 742
8. C. Takagi, M. Sukeda, H.S. Kim, Y. Wataya, S. Yabe, Y. Kitade, A. Matsuda, and S. Shuto Org. Biomol. Chem. 3 2005 1245 1251
9. A.D. Borthwick, B.E. Kirk, K. Biggadike, A.M. Exall, S. Butt, S.M. Roberts, D.J. Knight, J.A.V. Coats, and D.M. Ryan J. Med. Chem. 34 1991 907 914
10. T. Nakayama, Y. Matsumura, Y. Morizawa, A. Yasuda, K. Uchida, H. Takase, Y. Murakami, S. Atarashi, T. Ikeuchi, and Y. Osada Chem. Pharm. Bull. 42 1994 183 187
11. L.S. Jeong, H.R. Moon, J.G. Park, D.H. Shin, W.J. Choi, K.M. Lee, H.O. Kim, M.W. Chun, H.D. Kim, and J.H. Kim Nucleosides Nucleotides Nucleic Acids 22 2003 589 592
12. Y.Y. Yang, W.D. Meng, and F.L. Qing Org. Lett. 6 2004 4257 4259
13. T.C. Rosen, E. De Clercq, J. Balzarini, and G. Haufe Org. Biomol. Chem. 2 2004 229 237
14. H.O. Kim, S.J. Yoo, H.S. Ahn, W.J. Choi, H.R. Moon, K.M. Lee, M.W. Chun, and L.S. Jeong Bioorg. Med. Chem. Lett. 14 2004 2091 2093
15. H.R. Moon, H.J. Lee, H.R. Kim, K.M. Lee, S.K. Lee, H.O. Kim, M.W. Chun, and L.S. Jeong Bioorg. Med. Chem. Lett. 14 2004 5641 5644
16. For a leading reference see: X.Q. Yin, and S.W. Schneller Tetrahedron 61 2005 1839 1843
17. K. Laumen, E.H. Reimerdes, M. Schneider, and H. Gorisch Tetrahedron Lett. 26 1985 407 410
18. K. Laumen, and M. Schneider Tetrahedron Lett. 25 1984 5875 5878
19. K.L. Seley, S.W. Schneller, D. Rattendi, and C.J. Bacchi J. Med. Chem. 40 1997 622 624
20. For example, S.M. Siddiqi, X. Chen, S.W. Schneller, S. Ikeda, R. Snoeck, G. Andrei, J. Balzarini, and E. De Clercq J. Med. Chem. 37 1994 551 554
21. M. Tuncbilek, and S.W. Schneller Bioorg. Med. Chem. 11 2003 3331 3334
22. A. Roy, S.W. Schneller, K.A. Keith, C.B. Hartline, and E.R. Kern Bioorg. Med. Chem. 13 2005 4443 4449
23. X.Q. Yin, and S.W. Schneller Tetrahedron Lett. 11 2005 1927 1929
24. M. Matsuumi, M. Ito, and Y. Kobayashi Synlett 2002 1508 1510
25. V.P. Rajappan, X.Q. Yin, and S.W. Schneller Tetrahedron 58 2002 9889 9895
26. M. Yang, W. Ye, and S.W. Schneller J. Org. Chem. 69 2004 3993 3996
27. G.V.B. Madhavan, and J.C. Martin J. Org. Chem. 51 1986 1287 1293
28. For 3 : [ α ] D 23.4 -54.4 (c 0.149, DMSO).
29. H. Nakashima, M. Sato, T. Taniguchi, and K. Ogasawara Synthesis 6 2000 817 823
30. V.P. Rajappan, V.R. Hegde, and S.W. Schneller Syn. Commun. 31 2001 2849 2854
31. S.D. Patil, S.W. Schneller, M. Hosoya, R. Snoeck, G. Andrei, J. Balzarini, and E. De Clercq J. Med. Chem. 35 1992 3372 3377
32. 3: C, 44.61; H, 4.49; N, 26.01. Found: C, 44.49; H, 4.58; N, 25.72.
33. For 5 : [ α ] D 23.2 -16.5 (c 0.025, DMSO).
34. X.Q. Yin, V.P. Rajappan, A. Roy, and S.W. Schneller Syn. Commun. 33 2003 1477 1481