A new synthetic route to indoloquinones: Formal synthesis of ellipticine

Synlett

Volumn , Issue 6, 2005, Pages 994-996

  Mal, Dipakranjan ^a   Senapati, Bidyut K ^a   Pahari, Pallab ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Anionic cycloaddition; Indoles; Quinones

Indexed keywords

ELLIPTICINE; ETHER DERIVATIVE; FUROINDOLONE; INDOLE DERIVATIVE; INDOLOQUINONE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

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

EID: 17144385093     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864826     Document Type: Article

References (42)

1. Goodwin, S.; Smith, A. F.; Horning, E. C. J. Am. Chem. Soc. 1959, 81, 1903.
2. Dalton, L. K.; Demerac, S.; Elmes, B. C.; Lode, J. W.; Swan, J. M.; Teitei, T. Aust. J. Chem. 1967, 20, 2715.
3. (a) Knolker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
4. (b) Gribble, G. W. Synlett 1991, 289.
5. (c) Miki, Y.; Tsuzaki, Y.; Hibino, H.; Aoki, Y. Synlett 2004, 2206.
6. (d) Haider, N.; Sotelo, E. Chem. Pharm. Bull. 2002, 50, 1479.
7. (e) Ashcroft, W. R.; Dalton, L.; Beal, M. G.; Humphrey, G. L.; Joule, J. A. J. Chem. Soc., Perkin Trans. 1 1983, 2409.
8. (f) Diaz, M.; Cobas, A.; Guitian, E.; Castedo, L. Eur. J. Org. Chem. 2001, 4543.
9. (g) Ishikura, M.; Hino, A.; Yaginuma, T.; Agata, I.; Katagiri, N. Tetrahedron 2001, 56, 193.
10. (h) Fernadez, M.; Barcia, C.; Estevez, J. C.; Estevez, R. J.; Castedo, L. Synlett 2004, 267.
11. (i) Miller, R. B.; Dugar, S. Tetrahedron Lett. 1989, 30, 297.
12. Husson, H.-P. In The Alkaloids, Chemistry and Pharmacology, Vol.26; Brossi, A., Ed.; Academic Press, Inc.: Orlando, 1985, Chap.1, 1-51.
13. Richards, R. W.; Rothschild, J. M.; Willis, A. C.; De Chazal, N. M.; Kirk, J.; Kirk, K.; Saliba, K.; Smith, G. D. Tetrahedron 1999, 55, 13513.
14. Bernardo, P. H.; Chai, C. L. L.; Heath, G. A.; Mahon, P. J.; Smith, G. D.; Waring, P.; Wilkes, B. A. J. Med. Chem. 2004, 47, 4958.
15. Luo, Y.-L.; Chou, T.-C.; Cheng, C. C. J. Heterocycl Chem. 1996, 33, 113.
16. Sissouma, D.; Collet, S. C.; Guingant, A. Y. Synlett 2004, 2612.
17. (a) Ketcha, D. M.; Gribble, G. W. J. Org. Chem. 1985, 50, 5451.
18. (b) Bernardo, P. H.; Chai, C. L. L.; Elix, J. A. Tetrahedron Lett. 2002, 43, 2939.
19. (c) Kelly, T. R.; Zhao, Y.; Cavero, M.; Torneiro, M. Org. Lett. 2000, 2, 3735.
20. (d) Miki, Y.; Hachiken, H.; Yanase, N. J. Chem. Soc., Perkin Trans. 1 2001, 2213.
21. (a) Macias-Ruvalcaba, N.; Cuevas, G.; Gonzalez, I.; Aguilar-Martinez, M. J. Org. Chem. 2002, 67, 3673.
22. (b) Knölker, H.-J.; O'Sullivan, N. Tetrahedron 1994, 50, 10893.
23. (c) Bittner, S.; Krief, P.; Massil, T. Synthesis 1991, 215.
24. (a) Mal, D.; Pal, R.; Murty, K. V. S. N. J. Chem. Soc., Chem. Commun. 1992, 821.
25. (b) Majumdar, G.; Pal, R.; Murty, K. V. S. N.; Mal, D. J. Chem. Soc., Perkin Trans. 1 1994, 309.
26. (c) Hazra, N. K.; Roy, H. N.; Adhikary, S.; Mal, D. Tetrahedron 1997, 53, 2177.
27. (d) Hauser, F. M.; Dorsch, W. A.; Mal, D. Org. Lett. 2002, 4, 2237.
28. (a) Hassner, A.; Stumer, C. Organic Syntheses Based on Name Reactions; Elsevier Science Ltd.: UK, 2002, 153.
29. (b) Hauser, F. M.; Rhee, R. P. J. Org. Chem. 1978, 43, 178.
30. (c) Kraus, G. A.; Sujimoto, H. Tetrahedron Lett. 1978, 19, 2263.
31. (d) Freskos, J. N.; Morrow, G. W.; Swenton, J. S. J. Org. Chem. 1985, 50, 805.
32. (e) Brade, W.; Vasella, A. Helv. Chim. Acta 1989, 72, 1649.
33. (f) Matsumoto, T.; Yamaguchi, H.; Tanabe, M.; Yasui, Y.; Suzuki, K. Tetrahedron Lett. 2000, 41, 8393.
34. (g) Couladouros, E. A.; Strongilos, A. T.; Papageorgiou, V. P.; Plyta, Z. F. Chem. Eur. J. 2002, 8, 1795.
35. (h) Mal, D.; Patra, A.; Roy, H. Tetrahedron Lett. 2004, 54, 7895.
36. Harradence, R. H.; Lions, F. J. Proc. R. Soc. N. S. W. 1939, 72, 209.
37. Mitchell, A. S.; Russell, R. A. Tetrahedron 1997, 53, 4387.
38. Dodsworth, D. J.; Calcagno, M.; Ehrmann, E. U.; Devadas, B.; Sammes, P. G. J. Chem. Soc., Perkin Trans. 1 1981, 2120.
39. Khanpure, S. P.; Biehl, E. R. Heterocycles 1988, 27, 2643.
40. (a) Taylor, D. A.; Baradarani, M. M.; Martinez, S. J.; Joule, J. A. J. Chem. Res., Synop. 1979, 387.
41. (b) Taylor, D. A.; Baradarani, M. M.; Martinez, S. J.; Joule, J. A. J. Chem. Res., Synop. 1979, 4801.
42. (c) Saulnier, M. G.; Gribble, G. W. J. Org. Chem. 1983, 48, 2690.