Synthesis of didemnolines A-D, N9-substituted β-carboline alkaloids from the marine ascidian Didemnum sp.

Tetrahedron

Volumn 55, Issue 4, 1999, Pages 935-942

  Schumacher, Robert W ^a   Davidson, Bradley S ^b  

^a UTAH STATE UNIVERSITY   (United States)

^b UNIVERSITY OF HAWAII   (United States)

Author keywords

Alkaloids; Imidazoles; Natural Products

Indexed keywords

ALKALOID; BETA CARBOLINE DERIVATIVE; DIDEMNOLINE A; DIDEMNOLINE B; DIDEMNOLINE C; DIDEMNOLINE D; EUDISTOMIN DERIVATIVE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; PRIORITY JOURNAL; SPECTROSCOPY; SYNTHESIS;

ASCIDIA; DIDEMNUM SP.;

EID: 0033593280     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01100-4     Document Type: Article

References (33)

1. Davidson, B. S. Chem Reviews 1993, 93, 1771.
2. Molinski, T. F. Chem Reviews 1993, 93, 1825.
3. Rinehart, K. L., Jr.; Kobayashi, J.; Harbour, G. C.; Hughes, R. G., Jr.; Mizsak, S. A.; Scahill, T. A. J. Am. Chem. Soc. 1984, 106, 1524.
4. Kobayashi, J.; Harbour, G. C.; Gilmore, J.; Rinehart, K. L., Jr. J. Am. Chem. Soc. 1984, 106, 1526.
5. Rinehart, K. L., Jr.; Kobayashi, J.; Harbour, G. C.; Gilmore, J.; Mascal, M.; Holt, T. G.; Shield, L. S.; Lafargue, F. J. Am. Chem. Soc. 1987, 109, 3378.
6. Kinzer, K. F.; Cardellina II, J. H. Tetrahedron Lett. 1987, 28, 925.
7. Lake, R. J.; Brennan, M. M.; Blunt, J. D.; Munro, M. H. G. Tetrahedron Lett. 1988, 29, 2255.
8. Blunt, J. W.; Lake, R. J.; Munro, M. H. G. Tetrahedron Lett. 1987, 28, 1825.
9. Lake, R. J.; Blunt, J. W.; Munro, M. H. G. Aust. J. Chem. 1989, 42, 1201.
10. Lake, R. J.; McCombs, J. D.; Blunt, J. W.; Munro, M. H. G.; Robinson, W. T. Tetrahedron Lett. 1988, 29, 4971.
11. Kobayashi, J.; Nakamura, H.; Ohizumi, Y.; Hirata, Y. Tetrahedron Lett. 1986, 27, 1191.
12. Kobayashi, J.; Cheng, J.; Ohta, T.; Nozoe, S.; Ohizumi, Y.; Sasaki, T. J. Org. Chem. 1990, 55, 3666.
13. Murata, O.; Shigemori, H.; Ishibashi, M.; Sugama, K.; Hayashi, K.; Kobayashi, J. Tetrahedron Lett. 1991, 32, 3539.
14. Debitus, C.; Laurent, D.; Pais, M. J. Nat. Prod. 1988, 51, 799.
15. Searle, P. A.; Molinski, T. F. J. Org. Chem. 1994, 59, 6600-6605.
16. Foderaro, T. A.; Barrows, L. R.; Lassota, P.; Ireland, C. M. J. Org. Chem. 1997, 62, 6064-6065.
17. Schumacher, R. W.; Davidson, B. S. Tetrahedron 1995, 51, 10125-10130.
18. Iddon, B. J. Chem. Soc. Perkin Trans. 1, 1983, 737.
19. Iddon, B.; Khan, N. J. Chem. Soc, Perkin Trans. 1, 1987, 1445.
20. Iddon, B. J. Chem. Soc. Perkin Trans. 1, 1987, 1453.
21. Groziak, M. P.; Wei, L. J. Org. Chem. 1991, 56, 4296.
22. Ley, R. J. Org. Chem. 1991, 56, 5739.
23. Groziak, M. P.; Wei, L. J. Org. Chem. 1992, 57, 3776.
24. Iddon, B.; Ngochindo, R. I. Heterocycles 1994, 38, 2487.
25. Iddon, B.; Petersen, A. K.; Becher, J.; Christensen, N. J. J. Chem. Soc. Perkin Trans. 1, 1995, 1475.
26. Ayer, W. A.; Craw, P. A.; Ma, Y.; Miao, S. Tetrahedron 1992, 48, 2919.
27. Severin, T.; Bruck, B. Angew. Chem. 1965, 77 3847.
28. Varma, R. S.; Kabalka, G. W. Synth. Commun. 1985, 15, 843.
29. Ho, B. T.; Walker, K. E. Org. Synth. Col. Vol. VI, 1988, 965.
30. Snyder, H. R.; Hansch, C. H.; Katz, L.; Parmerter, S. M.; Apaeth, E. C. J. Am. Chem. Soc. 1948, 70, 219 and references cited therein.
31. Still, I. W. J.; McNulty, J. Heterocycles 1989, 29, 2057.
32. Still, W. C.; Kahn, M.; Mitra, J. J. Org. Chem. 1978, 43, 2923.
33. Stenio, K. E.; Wahlberg, K.; Wahren, R. Acta Chem. Scand. 1973, 27, 2179.