Novel synthesis of o-naphthothiophenequinone derivatives via regioselective Diels-Alder reaction

Tetrahedron

Volumn 61, Issue 38, 2005, Pages 9097-9101

  Shen, Yu Dong ^a   Wu, Hai Qiang ^a   Zhang, Sheng Ling ^a   Bu, Xian Zhang ^a   An, Lin Kun ^a   Huang, Zhi Shu ^a   Liu, Pei Qing ^a   Gu, Lian Quan ^a   Li, Yue Ming ^b   Chan, Albert S C ^b  

^a SUN YAT SEN UNIVERSITY   (China)

^b HONG KONG POLYTECHNIC UNIVERSITY   (Hong Kong)

Author keywords

Diels Alder; IBX; o Naphthothiophenequinone; Regioselectivity

Indexed keywords

ALKADIENE; QUINONE DERIVATIVE;

AROMATIZATION; ARTICLE; DIELS ALDER REACTION; ELECTRON; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

BETULACEAE;

EID: 23944524532     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.07.036     Document Type: Article

References (39)

1. G.Y. Zhou, B.L. Zhao, J.W. Hou, G.E. Ma, and W.J. Xin Pharmacol. Res. 40 1999 487 491
2. W. Zhou, and T.J. Ruigrok Am. J. Chin. Med. 18 1990 19 24
3. X.C. Weng, and M.H. Gordon J. Agric. Food Chem. 40 1992 1331 1336
4. T.B. Ng, F. Liu, and Z.T. Wang Life Sci. 66 2000 709 723
5. S.Y. Ryu, C.O. Lee, and S.U. Choi Planta Med. 63 1997 339 342
6. S. Park, J.-S. Song, D.-K. Lee, and C.-H. Yang Bull. Korean Chem. Soc. 20 1999 925 928
7. W.L. Chang, and C.F. Chen Am. J. Chin. Med. 19 1991 207 212
8. Y. Yoon, Y.O. Kim, W.K. Jeon, H.J. Park, and H.J. Sung J. Ethnopharmacol. 68 1999 121 127
9. H.J. Sung, S.M. Choi, Y. Yoon, and K.S. An Exp. Mol. Med. 31 1999 174 178
10. H.M. Chang, K.Y. Chui, F.W.L. Tan, Y. Yang, Z.P. Zhong, C.M. Lee, H.L. Sham, and N.C. Wong J. Med. Chem. 34 1991 1675 1692 and references cited therein
11. (a) Frydman, B. J.; Witiak, D. T.; Sun, J. S.; Geiser, A. H. Patent no. US005969163A.
12. C.E.M Carvalho, V.F. Ferreira, A.V. Pinto, M.C.F.R. Pinto, and W. Harrison Dyes Pigm. 52 2002 209 214 and references cited therein
13. C.Y. Ting, C.T. Hsu, J.S. Su, T.Y. Chen, W.Y. Tarn, Y.H. Kuo, W.P. Jacqueline, L.F. Liu, and J. Hwang Biochem. Pharmacol. 66 2003 1981 1991 and references cited therein
14. K. Ngampong, K. Bonsong, S. Pongpun, S. Chak, L. Suwaporn, N. Momad, P. Suppachai, P. Suratsawadee, and K. Palangpon Bioorg. Med. Chem. 11 2003 3179 3191
15. Y. Tezuka, R. Kasimu, P. Basnet, T. Namba, and S. Kadota Chem. Pharm. Bull. 45 1997 1306 1311
16. G. Honada, Y. Koezuka, and M. Tabata Chem. Pharm. Bull. 36 1988 408
17. M. Onitsuka, M. Fujiu, N. Shinma, and H.B. Maruyama Chem. Pharm. Bull. 31 1983 1670
18. A.R. Lee, W.L. Wu, W.L. Chang, H.C. Lin, and M.L. King J. Nat. Prod. 50 1987 157
19. D.Y. Shin, H.S. Kim, K.H. Min, S.S. Hyun, S.A. Kim, H. Huh, E.C. Choi, Y.H. Choi, J. Kim, S.H. Choi, W.B. Kim, and Y.G. Suh Chem. Pharm. Bull. 48 2000 1805 1806
20. H.M. Chang, K.Y. Chui, F.W.L. Tan, Y. Yang, Z.P. Zhong, C.M. Lee, H.L. Sham, and H.N.C. Wang J. Med. Chem. 34 1991 1675 1692
21. A.P. Krapcho, M.E. Petry, and M.P. Hacker J. Med. Chem. 33 1990 2651 2655
22. L.J. Huang, S.C. Kuo, C.Y. Perng, Y.H. Chao, T.S. Wu, A.T. McPhail, A. Mauger, H.H. Cheng, and K.H. Lee Bioorg. Med. Chem. Lett. 8 1998 2763 2768
23. P.A. Urbanek, S.J. Suchard, G.B. Steelman, K.S. Knappenberger, L.A. Sygowski, C.A. Veale, and M.J. Chapdelaine J. Med. Chem. 44 2001 1777 1793
24. M.O.F. Goulart, C.L. Zani, J. Tonholo, L.R. Freitas, F.C. Abreu, A.B. Oliveira, D.S. Raslan, S. Starling, and E. Chiari Bioorg. Med. Chem. Lett. 7 1997 2043 2048
25. C.L. Zani, E. Chiari, A.U. Krettli, S.M.F. Murta, M.L. Cunningham, A.H. Fairlamb, and A.J. Romanha Bioorg. Med. Chem. Lett. 5 1997 2185 2192
26. J. Valderrama, A. Fourent, C. Valderrama, S. Bastias, C. Astudillo, A. Rojas de Arias, A. Inchausti, and G. Yaluff Chem. Pharm. Bull. 47 1999 1221 1226
27. R.A. Tapia, L. Alegria, C.D. Pessoa, C. Salas, M.J. Cortés, J.A. Valderrama, M.E. Sarciron, F. Pautet, N. Walchshofer, and H. Fillon Bioorg. Med. Chem. 11 2003 2175 2182
28. (a) Gu, L. Q.; Bu, X. Z.; Ma, L. PCT CN 0100861, May 24, 2001.
29. X.Z. Bu, Z.S. Huang, M. Zhang, L. Ma, G.W. Xiao, and L.Q. Gu Tetrahedron Lett. 42 2001 5737 5740
30. A. Lin-Kun, B. Xian-Zhang, W. Hai-Qiang, G. Xin-Dong, M. Lin, and G. Lian-Quan Tetrahedron 58 2002 10315 10321
31. J.K. Ray, S. Cupta, G.K. Kar, B.C. Roy, J.M. Lin, and S. Amin J. Org. Chem. 65 2000 8134 8138
32. Brandao, M. A. F.; Braga de Oliveira, A.; Snieckus, V. Dep. Quim., Univ. Fed. Minas Gerais, Belo Horizonte, Brazil. Tetrahedron Lett. 1993, 34, 2437-2440.
33. C.D. Jones, M.G. Jevnikar, and A.J. Pike J. Med. Chem. 27 1984 1057 1066
34. J.T. Vicenzi, T.Y. Zhang, R.L. Robey, and C.A. Alt Org. Process Res. Dev. 3 1999 56 59
35. H. Zimmer, D.C. Lankin, and S.W. Horgan Chem. Rev. 71 1971 229 246
36. D. Magdziak, A.A. Rodriguez, R.W.V.D. Water, and T.R.R. Pettus Org. Lett. 4 2002 285 288
37. D. Gördes, A.J. Wangelin, S. Klaus, H. Neumann, D. Strübing, S. Hübner, H. Jiao, W. Baumann, and M. Beller Org. Biomol. Chem. 2 2004 845 851
38. 2=0.1817 ([I>2σ(I)]), 0.2224 (all data). Crystallographic data for the structures in this paper have been deposited with the Cambridge crystallographic data centre as supplementary publication numbers CCDC 267293. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 1223 336033 or e-mail: eposit@ccdc.cam.ac.uk ].
39. R. Bloch, and G.N. Chaptal J. Org. Chem. 59 1994 4162 4169