Isomers of neplanocin A and 2′-deoxyneplanocin A possessing a C-1′/C-6′ double bond

Tetrahedron Letters

Volumn 46, Issue 11, 2005, Pages 1927-1929

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

^a AUBURN UNIVERSITY   (United States)

Author keywords

Antiviral; Carbocyclic nucleosides; Epoxide ring opening; Neplanocin analogs

Indexed keywords

2' DEOXYNEPLANOCIN A; CYCLOPENTENE DERIVATIVE; NEPLANOCIN A; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ISOMERISM; STRUCTURE ANALYSIS;

EID: 13944251421     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.01.061     Document Type: Article

References (27)

1. V.E. Marquez Adv. Antivir. Drug Des. 2 1996 89 146
2. M. Ferrero, and V. Gotor Chem. Rev. 100 2000 4319 4347
3. E. De Clercq Antimicrob. Agents Chemother. 28 1985 84 89
4. M. Bray, J.L. Raymond, T. Geisbert, and R.O. Baker Antivir. Res. 55 2002 151 159
5. V.E. Marquez, P. Russ, R. Alonso, M.A. Siddiqui, S. Hernandez, C. George, M.C. Nicklaus, F. Dai, and H. Ford Jr. Helv. Chim. Acta 82 1999 2119 2129
6. M.T. Crimmins, B.W. King, W.J. Zuercher, and A.L. Choy J. Org. Chem. 65 2000 8499 8509
7. Ref. 5b establishes precedence for this atom numbering
8. Y. Xu, K. Kino, and H Sugiyama J. Biomol. Struct. Dyn. 20 2002 437 446
9. 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 reported a small amount (3%) of a racemic C-1′/C-6′ alkenic compound accompanying the synthesis of an α-fluoroaristeromycin derivative
10. K. Biggadike, A.D. Borthwick, and A.M. Exall J. Chem. Soc., Chem. Commun. 1990 458 459 mentioned the low yield of a protected carbathymidine arising during their preparation of the pyrimidine analog of 2′-deoxyneplanocin A
11. K.-H. Altmann, M.-O. Bévierre, A. De Mesmaeker, and H.E. Moser Bioorg. Med. Chem. Lett. 5 1995 431 436
12. K.L. Seley, S.W. Schneller, D. Rattendi, S. Lane, and C.J. Bacchi J. Med. Chem. 40 1997 625 629
13. H. Ovaa, B. Lastdrager, J.D.C. Codée, G.A. van der Marel, H.S. Overkleeft, and J.H. van Boom J. Chem. Soc., Perkin Trans. 1 2002 2370 2377
14. A.B. Cheikh, L.E. Craine, S.G. Recher, and J. Zemlicka J. Org. Chem. 53 1988 929 936
15. H.B. Henbest, and R.A.L. Wilson J. Chem. Soc. 1957 1958 1965
16. Yin, X.; Schneller, S.W., unpublished results
17. HRMS for compound 3, 263.1014 (calcd 263.1018)
18. satisfactory microanalytical data was obtained for compounds 3 and 4
19. 6) δ 161.6, 158.4, 154.7, 143.9, 143.3, 125.0, 124.5, 77.9, 76.4, 67.3, 57.8
20. 6) δ 156.0, 152.3, 150.1, 149.7, 139.5, 123.4, 119.2, 76.6, 72.2, 64.2, 58.6
21. X. Yin, and S.W. Schneller Tetrahedron 60 2004 3451 3455
22. M. Matsuumi, M. Ito, and Y. Kobayashi Synlett 2002 1508 1510
23. K. Biggadike, A.D. Borthwick, A.M. Exall, B.E. Kirk, S.M. Roberts, and P. Youds J. Chem. Soc., Chem. Commun. 1987 1083 1084
24. 6) δ 156.2, 153.1, 148.2, 148.1, 138.9, 133.1, 119.3, 116.7, 70.6, 62.5, 56.3, 41.1. Satisfactory microanalytical data was obtained for compound 4
25. 6) δ 8.13 (s, 1H), 7.97 (s, 1H), 7.17 (br, 2H), 5.75 (d, 1H, H-6′), 5.64 (m, 1H), 5.06 (d, 1H), 4.85-5.0 (m, 2H), 4.15 (br, 2H), 2.2-2.4 (m, 2H)
26. K. Fukukawa, T. Ueda, and T. Hirano Chem. Pharm. Bull. 31 1983 1842 1847
27. B.M. Trost, R. Madsen, S.D. Guile, and B. Brown J. Am. Chem. Soc. 122 2000 5947 5956