Preliminary studies on the incorporation of sugars into naphthoquinones: Synthesis of (1R,2S,3S,4R,4aS,11bS)-2-(benzyloxy)-1,2,3,4,4a,5-hexahydro-1,3,4- trihydroxy-11bH-benzo[b]carbazole-6,11-dione

Tetrahedron Asymmetry

Volumn 16, Issue 1, 2005, Pages 11-14

  Otero, José M ^a   Barcia, José C ^a   Estévez, Juan C ^a   Estévez, Ramón J ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; 2 (BENZYLOXY) 1,2,3,4,4A,5 HEXAHYDRO 1,3,4 TRIHYDROXY 11B BENZO[B]CARBAZOLE 6,11 DIONE; 2 LITHIUM 1,4 DIMETHOXYNAPHTHALENE; 3 (BENZYLOXY) 5 (1,4 DIMETHOXYNAPHTHALEN 2 YL) 1,2,4 TRIHYDROXY 6 NITROCYCLOHEXANE; 3 O BENZYL 5,6 DIDEOXY 1,2 O ISOPROPYLIDENE 6 NITRO ALPHA DEXTRO XYLOHEX 5 ENEFURANOSE; 3 O BENZYL 5,6 DIDEOXY 5 C (1,4 DIMETHOXYNAPHTHALEN 2 YL) 6 NITRO BETA LEVO IDOFURANOSE; CARBAZOLE DERIVATIVE; FURAN DERIVATIVE; GLUCOSE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOSELECTIVITY; MICHAEL ADDITION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 12344328311     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.11.045     Document Type: Article

References (52)

1. R.H. Thomson Naturally Occurring Quinones 4th ed. 1997 Chapman and Hall London/New York
2. S. Spyroudis Molecules 5 2000 1291
3. C.C. Cheng G.P. Ellis G.B. West Progress in Medicinal Chemistry, Structural Aspects of Antineoplastic Agents-A New Approach Vol. 25 1988 Elsevier Amsterdam
4. Y.-L. Luo, T.-C. Chou, and C.C. Cheng J. Heterocycl. Chem. 33 1996 113
5. H.-J. Knölker, and K.R. Reddy Chem. Rev. 102 2002 4303 4427
6. E. Martinez, L. Martinez, M. Treus, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron 56 2000 6023
7. A. Martinez, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 41 2000 2365
8. H.-X. Chang, T.-C. Chou, N. Savaraj, L.F. Liu, C. Yu, and C.C. Cheng J. Med. Chem. 42 1999 405
9. E. Martinez, L. Martinez, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 39 1998 2175
10. A.M. Echavarren, N. Tamayo, O. De Frutos, and A. Garcia Tetrahedron 53 1997 16835
11. K. Yoshida, Y. Yamanaka, and Y. Euno Chem. Lett. 1994 2051
12. C.C. Cheng, Q. Dong, D.F. Liu, Y.L. Luo, L.F. Liu, A.Y. Chen, C. Yu, N. Savaraj, and T.C. Chou J. Med. Chem. 36 1993 4108
13. A.R. Forrester, A.S. Ingram, I.L. John, and R.H. Thomson J. Chem. Soc., Perkin Trans. 1 1975 1115
14. G. Qabaja, and G.B. Jones J. Org. Chem. 65 2000 7187
15. G. Qabaja, E.M. Perchellet, J.-P. Perchellet, and G.B. Jones Tetrahedron Lett. 41 2000 3007
16. E. Martinez, L. Martinez, M. Treus, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron 56 2000 6023
17. S.-I. Mohri, M. Stefinovic, and V. Snieckus Can. J. Chem. 62 1997 7072
18. A.M. Echavarren, N. Tamayo, and D.J. Cardenas J. Org. Chem. 59 1994 6075
19. N. Tamayo, A.M. Echavarren, and M.C. Paredes J. Org. Chem. 56 1991 6488
20. T.C. McKenzie, and W.B. Choi Synth. Commun. 19 1989 1523
21. M. Watanabe, M. Date, and S. Furukawa Chem. Pharm. Bull. 37 1989 292
22. S. Arai, H. Tsuge, M. Oku, M. Miura, and T. Shioiri Tetrahedron 58 2002 1623
23. F. Coppa, F. Fontana, E. Lazzarini, and F. Minisci Chem. Lett. 7 1992 1299
24. S. Arai, M. Oku, M. Miura, and T. Shioiri Synlett 11 1998 1201
25. S. Colonna, N. Gaggero, A. Manfredi, M. Spadoni, L. Casella, G. Carrea, and P. Pasta Tetrahedron 44 1988 5169
26. S. Colonna, A. Manfredi, R. Annunziata, and M. Spadoni Tetrahedron 43 1987 2157
27. H. Pluim, and H. Wynberg J. Org. Chem. 45 1980 2498
28. K. Krohn, H.H. Ostermeyer, and K. Tolkiehn Chem. Ber. 112 1979 2640
29. D.M. Fieldgate, and D. Woodcock Pestic. Sci. 4 1973 193
30. L.F. Fieser, E. Berliner, F.J. Bondhus, F.C. Chang, W.G. Dauben, M.G. Ettlinger, G. Fawaz, M. Fileds, C. Heidelberger, H. Heymann, W.R. Vaughan, A.G. Wilson, E. Wilson, M. Wu, M.T. Leffler, K.E. Hamlin, E.J. Matson, E.E. Moore, M.B. Moore, and H.E. Zaugg J. Am. Chem. Soc. 70 1948 3186
31. P.J. O'Sullivan, R. Moreno, and W.S. Murphy Tetrahedron Lett. 33 1992 535
32. O. Noboru H. Feuer The Nitro Group in Organic Synthesis Organic Nitro Chemistry Series 2001 Wiley-VCH
33. L.C.R. Henry Acad. Sci. Paris 120 1895 1265
34. F.A. Luzzio Tetrahedron 57 2001 915
35. O. Noboru H. Feuer The Nitro Group in Organic Synthesis Organic Nitro Chemistry Series 2001 Wiley-VCH Chapter 2
36. R.S. Varma, and G.W. Kabalka Heterocycles 24 1986 2645
37. A.G.M. Barret, and G.G. Graboski Chem. Rev. 86 1986 751
38. M. Fernández, J.C. Barcia, J.C. Estévez, R.J. Estévez, and L. Castedo Synlett 2004 267
39. J.C. Barcia, J. Cruces, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 43 2002 5141
40. J. Cruces, E. Martinez, M. Treus, L.A. Martinez, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron 58 2002 3015
41. J.C. Estévez, R.J. Estevez, and L. Castedo Tetrahedron Lett. 34 1993 6479
42. R.G. Soengas, J.C. Estévez, and R.J. Estévez Tetrahedron: Asymmetry 14 2003 3955
43. R.G. Soengas, J.C. Estévez, and R.J. Estévez Org. Lett. 5 2003 4459
44. R.G. Soengas, J.C. Estévez, and R.J. Estévez Org. Lett. 5 2003 1423
45. R.G. Soengas, J.C. Estévez, and R.J. Estévez Tetrahedron: Asymmetry 14 2003 1653
46. P.A. Evans, and T.A. Brandt J. Org. Chem. 62 1997 5321
47. J. Bloomer, and W. Zheng Synth. Commun. 28 1998 2087
48. G.W.J. Fleet, and P.W. Smith Tetrahedron 43 1987 971
49. M. Funabashi, K. Kobayashi, and J. Yoshimura J. Org. Chem. 44 1979 1618
50. +-OH)
51. 1/2
52. S.J. Gould Chem. Rev. 97 1997 2499 2509