Synthesis of C11N5 Marine Sponge Alkaloids: (±)-Hymenin, Stevensine, Hymenialdisine, and Debromohymenialdisine

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 456-464

  Xu, Ying Zi ^a   Yakushijin, Kenichi ^a   Horne, David A ^a  

^a Columbia University ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; DEBROMOHYMENIALDISINE; HYMENIALDISINE; HYMENIN; STEVENSINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031019028     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9619746     Document Type: Article

References (32)

1. For reviews of marine alkaloids, see: (a) Christophersen, C. In The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 24, pp 25-111. (b) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124. (c) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75, and earlier reports.
2. For reviews of marine alkaloids, see: (a) Christophersen, C. In The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 24, pp 25-111. (b) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124. (c) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75, and earlier reports.
3. For reviews of marine alkaloids, see: (a) Christophersen, C. In The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 24, pp 25-111. (b) Kobayashi, J.; Ishibashi, M. In The Alkaloids: Chemistry and Pharmacology, Brossi, A., Ed.; Academic Press: New York, 1992; Vol. 41, pp 41-124. (c) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75, and earlier reports.
4. (a) Kobayashi, J.; Ohizumi Y.; Nakamura H.; Hirata, Y.; Wakamatsu, K.; Miyazawa, T. Experientia 1986, 42, 1064.
5. (b) Kobayashi, J.; Nakamura, H.; Ohizumi, Y. Experientia 1988, 44, 86.
6. Albizati, K. F.; Faulkner, D. J. J. Org. Chem. 1985, 50, 4163.
7. Nanteuil, G. D.; Ahond, A.; Guilhem, J.; Poupat, C.; Dau, E. T. H.; Potier, P.; Pusset, M.; Pusset, J.; Laboute, P. Tetrahedron 1985, 41, 6019.
8. Cimino, G.; DeRosa, S.; DeStefano, S.; Mazzarella, L.; Puliti, R.; Sodano, G. Tetrahedron Lett. 1982, 23, 767.
9. Kitagawa, I.; Kobayashi, M.; Kitanaka, K.; Kido, M.; Kyogoku, Y. Chem. Pharm. Bull. 1983, 31, 2321.
10. Schmitz, F. J.; Gunasekera, S. P.; Lakshmi, V.; Tillekeratne, L. M. V. J. Nat. Prod. 1985, 48, 47.
11. Pettit, G. R.; Herald, C. L.; Leet, J. E.; Gupta, R.; Schaufelberger, D. E.; Bates, R. B.; Clewlow, P. J.; Doubek, D. L.; Manfredi, K. P.; Rützler, K.; Schmidt, J. M.; Tackett, L. P.; Ward, F. B.; Brück, M.; Camou, F. Can. J. Chem. 1990, 68, 1621.
12. Sharma, G. M.; Buyer, J. S.; Pomerantz, M. W. J. Chem. Soc., Chem. Commun. 1980, 435.
13. 4 metabolite axinohydantoin (ref 8), isolated from Axinella sp. and Hymeniacidon sp., also possesses an α-monobromo pyrrole moiety.
14. D -15° (MeOH) has not been determined.
15. Xu, Y.-z.; Phan, G.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1994, 35, 351.
16. (a) Remers, W, A. In Heterocyclic Compounds: Indoles Part I; Houlihan, W. J., Ed.; Wiley-Interscience: New York, 1972; pp 66-70.
17. (b) Chadwick, D. J. In Comprehensive Heterocyclic Chemistry: The Structure, Reactions, Synthesis and Use of Heterocyclic Compounds; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: New York, 1984; Vol. 4; pp 206-209.
18. Bailey, D. M.; Johnson, R. E. J. Med. Chem. 1973, 16, 1300.
19. Gribble, G. W.; Switzer, F. L. Synth. Commun. 1987, 17, 377.
20. 3OD) δ 33.5 (t), 37.2 (t), 50.7 (d), 102.8 (s), 108.0 (s), 117.9 (dx2), 125.3 (s), 128.0 (s), 150.7 (s), 163.9 (s).
21. 3H for 7 d.
22. Ruasse, M.-F. Acc. Chem. Res. 1990, 23, 87.
23. 3-Debromostevensine (20) and 5-bromo-3-debromostevensine (21) were also obtained from the transbromination of 4′-bromohymenin (22). Xu, Y.-z.; Yakushijin, K.; Horne, D. A. Tetrahedron Lett. 1996, 37, 8121.
24. March, J. In Advanced Organic Chemistry, 4th ed.; John Wiley and Sons: New York, 1992; p 556.
25. (a) Ipso attack has been studied mostly for nitration, see March, J. In Advanced Organic Chemistry, 4th ed.; John Wiley and Sons: New York, 1992; p 458.
26. +, see Olah, G. A.; Meyer, M. W. J. Org. Chem. 1962, 27, 3464.
27. (c) For bromination of aromatic compounds facilitated by strong acids, see Bull. Chem. Soc. Jpn. 1994, 67, 1918.
28. Prager, R. H.; Tsopelas, C. Aust. J. Chem. 1990, 43, 367.
29. 1H NMR spectrum of debromohymenialdisine (4) in acidic media.
30. Anderson, H. J.; Lee, S. F. Can. J. Chem. 1956, 43, 409.
31. Baily, D. M.; Johnson, R. E.; Albertson, N. F. Org. Synth. 1971, 51, 100.
32. Annoura, H.; Tatsuoka, T. Tetrahedron Lett. 1995, 36, 413.