Synthesis of pyrrolo[4,3,2-de]quinolines from 6,7-dimethoxy-4-methylquinoline. Formal total syntheses of damirones A and B, batzelline C, isobatzelline C, discorhabdin C, and makaluvamines A-D

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 568-577

  Roberts, David ^a   Joule, John A ^a   Antonieta Bros, M ^b   Alvarez, Mercedes ^b  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

^b UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BATZELLINE C; CYTOTOXIC AGENT; DAMIRONE A; DAMIRONE B; DISCORHABDIN C; ISOBATZELLINE C; MAKALUVAMINE A; MAKALUVAMINE B; MAKALUVAMINE C; MAKALUVAMINE D; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0031017581     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961743z     Document Type: Article

References (42)

1. Märki, F.; Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1961, 83, 3341. Robinson, B.; Smith, G. F.; Jackson, A. H.; Shaw, D.; Frydman, B.; Deulofeu, V. Proc. Chem. Soc. (London) 1961, 310.
2. Märki, F.; Robertson, A. V.; Witkop, B. J. Am. Chem. Soc. 1961, 83, 3341. Robinson, B.; Smith, G. F.; Jackson, A. H.; Shaw, D.; Frydman, B.; Deulofeu, V. Proc. Chem. Soc. (London) 1961, 310.
3. Marine Nitrogen-Containing Heterocyclic Natural Products. 1. Structures and Syntheses of Compounds Containing Quinoline and/or Isoquinoline Units. Salas, M.; Alvarez, M; Joule, J. A. Heterocycles 1991, 32, 759. Marine Nitrogen-Containing Heterocyclic Natural Products. 2, Structures and Syntheses of Compounds Containing Indole Units, ibid. 1991, 32, 1391.
4. Marine Nitrogen-Containing Heterocyclic Natural Products. 1. Structures and Syntheses of Compounds Containing Quinoline and/or Isoquinoline Units. Salas, M.; Alvarez, M; Joule, J. A. Heterocycles 1991, 32, 759. Marine Nitrogen-Containing Heterocyclic Natural Products. 2, Structures and Syntheses of Compounds Containing Indole Units, ibid. 1991, 32, 1391.
5. Sakemi, S.; Sun, H. H.; Jefford, C. W.; Bernardinelli, G. Tetrahedron Lett. 1989, 30, 2517.
6. Sun, H. H.; Sakemi, S.; Burres, N.; McCarthy, P. J. Org. Chem. 1990, 55, 4964.
7. Stierle, D. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1131.
8. Copp, B. R.; Ireland, C. M.; Barrows, L. R. J. Org. Chem. 1991, 56, 4596.
9. 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. Barrows, L. R.; Radisky, D. C.; Copp, B. R.; Swaffer, D. S.; Kramer, R. A.; Warters, R. C.; Ireland, C. M. Anti-Cancer Drug Des. 1993, 8, 333. Ireland, C. M.; Radisky, D. C.; Barrows, L. R.; Kramer, R. A., US Patent 5,414,001 (Chem. Abstr. 1995, 123, 111835).
10. 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. Barrows, L. R.; Radisky, D. C.; Copp, B. R.; Swaffer, D. S.; Kramer, R. A.; Warters, R. C.; Ireland, C. M. Anti-Cancer Drug Des. 1993, 8, 333. Ireland, C. M.; Radisky, D. C.; Barrows, L. R.; Kramer, R. A., US Patent 5,414,001 (Chem. Abstr. 1995, 123, 111835).
11. 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. Barrows, L. R.; Radisky, D. C.; Copp, B. R.; Swaffer, D. S.; Kramer, R. A.; Warters, R. C.; Ireland, C. M. Anti-Cancer Drug Des. 1993, 8, 333. Ireland, C. M.; Radisky, D. C.; Barrows, L. R.; Kramer, R. A., US Patent 5,414,001 (Chem. Abstr. 1995, 123, 111835).
12. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. J. Org. Chem. 1986, 51, 5476. Perry, N. B.; Blunt, J. W.; Munro, M. H. G. Tetrahedron 1988, 44, 1727; Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R. J. Org. Chem. 1988, 53, 4127.
13. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. J. Org. Chem. 1986, 51, 5476. Perry, N. B.; Blunt, J. W.; Munro, M. H. G. Tetrahedron 1988, 44, 1727; Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R. J. Org. Chem. 1988, 53, 4127.
14. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. J. Org. Chem. 1986, 51, 5476. Perry, N. B.; Blunt, J. W.; Munro, M. H. G. Tetrahedron 1988, 44, 1727; Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R. J. Org. Chem. 1988, 53, 4127.
15. Kobayashi, J.; Cheng, J.-F.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T.; Lu, H.; Clardy, J. Tetrahedron Lett. 1987, 28, 4939. Cheng, J.-F.; Ohizumi, Y.; Wälchli, M. R.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1988, 53, 4621.
16. Kobayashi, J.; Cheng, J.-F.; Ishibashi, M.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T.; Lu, H.; Clardy, J. Tetrahedron Lett. 1987, 28, 4939. Cheng, J.-F.; Ohizumi, Y.; Wälchli, M. R.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1988, 53, 4621.
17. D'Ambrosia, M.; Guerriero, A.; Chiasera, G.; Pietra, F. Tetrahedron 1996, 55, 8899.
18. Wang, H.; Al-Said, N. H.; Lown, J. W. Tetrahedron Lett. 1994, 35, 4085.
19. Hester, J. B. J. Org. Chem. 1964, 29, 1158.
20. Hamabuchi, S.; Hamada, H.; Hironaka, A.; Somei, M. Heterocycles 1991, 32, 443.
21. Julia, M.; Huang, Y.; Igolen, J. C. R. Hebd. Seances Acad. Sci. 1967, 265, 110.
22. Lee, F. G. H.; Daly, J. W.; Manian, A. A. J. Med. Chem. 1969, 12, 321.
23. Gannon, W. F.; Benigni, J. D.; Suzuki, J.; Daly, J. W. Tetrahedron Lett. 1967, 1531.
24. Tao, X. L.; Nishiyama, S.; Yamamura, S. Chem. Lett. 1991, 1785.
25. Tao, X. L.; Cheng, J.-F; Nishiyama, S.; Yamamura, S. Tetrahedron 1994, 50, 2017.
26. Kita, Y.; Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem. Soc. 1992, 114, 2175.
27. Sadanandan, E. V.; Pillai, S. K.; Lakshmikantham, M. V.; Billimoria, A. D.; Culpepper, J. S.; Cava, M. P. J. Org. Chem. 1995, 60, 1800.
28. Sadanandan, E. V.; Cava, M. P. Tetrahedron Lett. 1993, 34, 2405.
29. Yamada, F.; Hamabuchi, S.; Shimizu, A.; Somei, M. Heterocycles 1995, 41, 1905.
30. Baumann, C.; Bröckelmann, M.; Fugmann, B.; Steffan, B.; Steglich, W.; Sheldrick, W. S. Angew. Chem., Int. Ed. Engl. 1993, 32, 1087.
31. White, J. D.; Yager, K. M.; Yakura, T. J. Am. Chem. Soc. 1994, 116, 1831.
32. Izawa, T.; Nishiyama, S.; Yamamura, S. Tetrahedron 1994, 50, 13593.
33. Hopmann, C.; Steglich, W. Liebigs Ann. 1996, 1117.
34. Balczewski, P.; Joule, J. A.; Estévez, C.; Alvarez, M. J. Org. Chem. 1994, 59, 4571. Estévez, C.; Venemalm, L.; Alvarez, M.; Joule, J. A. Tetrahedron 1994, 50, 7879.
35. Balczewski, P.; Joule, J. A.; Estévez, C.; Alvarez, M. J. Org. Chem. 1994, 59, 4571. Estévez, C.; Venemalm, L.; Alvarez, M.; Joule, J. A. Tetrahedron 1994, 50, 7879.
36. Roberts, D.; Venemalm, L.; Alvarez, M.; Joule, J. A. Tetrahedron Lett. 1994, 35, 7857; Roberts, D.; Alvarez, M.; Joule, J. A. Tetrahedron Lett. 1996, 37, 1509.
37. Roberts, D.; Venemalm, L.; Alvarez, M.; Joule, J. A. Tetrahedron Lett. 1994, 35, 7857; Roberts, D.; Alvarez, M.; Joule, J. A. Tetrahedron Lett. 1996, 37, 1509.
38. Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028.
39. Makosza, M.; Stalewski, J. Tetrahedron 1995, 51, 7263.
40. Manske, R. H. F.; Kulka, M. Org. React. 1953, 7, 59.
41. Vismara, E.; Fontana, F.; Minisci, F. Gazz. Chim. Ital. 1987, 117, 135.
42. Minter, D. E.; Stotter, P. L. J. Org. Chem. 1981, 46, 3965.