Facile synthesis of avicequinone-B natural product

Synthetic Communications

Volumn 32, Issue 20, 2002, Pages 3099-3105

  Rok Lee, Yong ^a   So Kim, Byung ^a   Ug Jung, Yong ^a   Soo Koh, Wha ^a   Soon Cha, Jin ^a   Woo Kim, Nam ^b  

^a Yeungnam University   (South Korea)

^b Kyungsan University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; AVICEQUINONE B; CERIUM NITRATE; FURONAPHTHOQUINONE; LAWSONE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; REACTION ANALYSIS; SYNTHESIS;

EID: 0036380512     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120013719     Document Type: Article

References (27)

1. (a) Komiyama, K.; Funayama, S.; Anraku, Y.; Ishibashi, M.; Takahashi, Y.; Omura, S. J. Antibiot. 1990, 43, 247;
2. (b) Closse, A.; Sigg, H.-P. Helv. Chim. Acta 1973, 56, 619;
3. (c) Sendl, A.; Chen, J.L.; Jolad, S.D.; Stoddart, C.; Rozhon, E.; Kernan, M. J. Nat. Prod. 1996, 59, 808.
4. (d) Gafner, S.; Wolfender, J.-L.; Nianga, M.; Stoeckli-Evans, H.; Hostettmann, K. Phytochemistry 1996, 42, 1315;
5. (e) Hayashi, T.; Smith, F.T.; Lee, K.-H. J. Med. Chem. 1987, 30, 2005;
6. (f) Inoue, K.; Chen, C.-C.; Inouye, H.; Kuriyama, K. J. Chem. Soc. Perkin Trans. 1 1981, 2764;
7. (g) Trani, A.; Dallanoce, C.; Panzone, G.; Ripamonti, F.; Goldstein, B.P.; Ciabatti, R. J. Med. Chem. 1997, 40, 967;
8. (h) Inouye, H.; Ueda, S.; Inoue, K.; Shiobara, Y. Phytochemistry 1981, 20, 1707;
9. (i) King, R.R.; Lawrence, H.; Calhoun, L.A. J. Agric. Food Chem. 1996, 44, 2849;
10. (j) Inoue, K.; Ueda, S.; Nayeshiro, H.; Inouye, H. Chem. Pharm. Bull. 1982, 30, 2265.
11. (a) Kingston, L.A.; Rao, M.M. Planta Med. 1980, 39, 230;
12. (b) Rao, M.M.; Kingston, D.G.I. J. Nat. Prod. 1982, 45, 600.
13. Heltzel, C.E.; Leslie Gunatilaka, A.A.; Glass, T.E.; Kingston, D.G.I. J. Nat. Prod. 1993, 56, 1500.
14. Ribeiro-Rodrigues, R.; dos Santos, W.G.; Oliverira, A.B.; Snieckus, V.; Zani, C.L.; Romanha, A. J. Bioorg. Medicinal Chem. Letter 1995, 5, 1509.
15. Abbott, B.J.; Hartwell, J.L.; Leiter, J.; Perdue, R.E.; Schepartz, S.A. Cancer Res. (Suppl.) 1967, 27, 190.
16. Ito, C.; Katsuno, S.; Kondo, Y.; Tan, H.T.-W.; Furukawa, H. Chem. Pharm. Bull. 2000, 48, 339.
17. Sutton, D.C.; Gillan, F.T.; Susic, M. Phytochemistry 1985, 24, 2877.
18. (a) Zani, C.L.; de Oliveira, A.B.; Sniekus, V. Tetrahedron Lett. 1987, 28, 6561;
19. (b) Perry, P.J.; Pavlidis, V.H.; Hadfield, J.A.; Coutts, I.G.C. J. Chem. Soc., Perkin Trans. 1 1995, 1085;
20. (c) Ghera, E.; Maurya, R.; Ben-David, Y. Tetrahedron Lett. 1986, 27, 3935;
21. (d) Kobayashi, K.; Shimizu, H.; Sasaki, A.; Suginome, H. J. Org. Chem. 1993, 58, 4614;
22. (e) Fujimoto, Y.; Eguchi, T.; Murasaki, C.; Ohashi, Y.; Kakinuma, K.; Takagaki, H.; Abe, M.; Inazawa, K.; Yamazaki, K.; Ikekawa, N.; Yoshikawa, O.; Ikekawa, T. J. Chem. Soc., Perkin Trans. 1 1991, 2323;
23. (f) Kang, W.-B.; Sekiya, T.; Toru, T.; Ueno, Y. J. Chem. Soc., Perkin Trans. 1 1990, 441.
24. (a) Koyanagi, J.; Yamamoto, K.; Nakayama, K.; Tanaka, A. J. Heterocyclic Chem. 1994, 31, 1303;
25. (b) Rivalle, C.; Bisagni, E.; Andre-Louisfert, J. Tetrahedron 1974, 30, 3193.
26. Lee, Y.R.; Kim, B.S.; Kim, D.H. Tetrahedron 2000, 56, 8845.
27. Kobayashi, K.; Uneda, T.; Tanaka, K.; Mori, M.; Tanaka, H.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 1998, 71, 1691.