Synthetic routes to pyrroloiminoquinone alkaloids. A direct synthesis of makaluvamine C

Journal of Organic Chemistry

Volumn 63, Issue 26, 1998, Pages 9846-9849

  Kraus, George A ^a   Selvakumar, Natesan ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DNA TOPOISOMERASE INHIBITOR; MAKALUVAMINE C; NATURAL PRODUCT; PYRROLOIMINOQUINONE ALKALOID; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDROGENATION; NITRATION; REDUCTION; SPONGE (PORIFERA);

EID: 0032567321     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981547n     Document Type: Article

References (30)

1. Molinski, T. F. Chem. Rev. 1993, 93, 1825.
2. Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632.
3. Venables, D. A.; Barrows, L. R.; Lassota, P.; Ireland, C. M. Tetrahedron Lett. 1997, 38, 721.
4. Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632.
5. Venables, D. A.; Barrows, L. R.; Lassota, P.; Ireland, C. M. Tetrahedron Lett. 1997, 38, 721.
6. White, J. D.; Yager, K. M.; Yakura, T. J. Am. Chem. Soc. 1994, 116, 1831.
7. Roberts, D.; Joule, J. A.; Bros, M. A.; Alvarez, M. J. Org. Chem, 1997, 62,568.
8. Yamada, F.; Hamabuchi, S.; Shimizu, A.; Somei, M. Heterocycles 1995, 41, 1905.
9. Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028.
10. Sadanandan, E. V.; Pillai, S. K; Lakshmikantham, M. V.; Billimoria, A. D.; Culpepper, J. S.; Cava, M. P. J. Org. Chem. 1995, 60, 1800.
11. Zhao, R.; Lown, J. W. Synth. Commun. 1997, 27, 2103.
12. Makoza, M.; Stalewski, J.; Maslennikova, O. S. Synthesis 1997, 1131.
13. Izawa, T.; Nishiyama, S.; Yamamura, S. Tetrahedron 1994, 50, 13593.
14. Kita, Y.; Watanabe, H.; Egi, M.; Saiki, T.; Fukuoka, Y.; Tohma, H. J. Chem. Soc., Perkin Trans, l 1998, 635 and references therein.
15. Kraus, G. A.; Selvakumar, N. Synlett 1998, 845.
16. Nucleophilic aromatic substitution: Terrier, F. Chem. Rev. 1982, 82, 77.
17. Makoza, M.; Stalewski, J.; Maslennikova, O. S. Synthesis 1997, 1131.
18. Piutti, A. Chem. Ber. 1896, 29, 84.
19. Krishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315.
20. Nishiyama, S.; Cheng, J.-F.; Tao, X. L.; Yamamura, S. Tetrahedron Lett. 1991, 32, 4151.
21. Bartlett, P. A.; Johnson, W. S. Tetrahedron Lett. 1970, 4459.
22. Olah, G. A.; Narang, S. C.; Balaram Gupta, B. G.; Malhotra, R. J. Org. Chem. 1979,44,1247.
23. Olah, G. A; Narang, S. C. Tetrahedron 1982, 38, 2225'.
24. Teuber, H.-J.; Hasselbach, M. Chem. Ber. 1959,92,674.
25. Teuber, H.-J. Org. Synth. 1972, 52, 88.
26. Yamada, F.; Hamabuchi, S.; Shimizu, A.; Somei, M. Heterocycles 1995,41,1905.
27. Teuber, H.-J.; Glosaucr, O. Chem. Ber. 1965,98,2939.
28. Izawa, T.; Nishiyama, S.; Yamamura, S. Tetrahedron 1994,50, 13593.
29. Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632.
30. f 0.46 in 1:1 MeOH: HOAc.