Synthetic and isolation studies related to the marine natural products (+)-elisabethadione and (+)-elisabethamine

Journal of Organic Chemistry

Volumn 72, Issue 6, 2007, Pages 1895-1900

  Dai, Xing ^a   Wan, Zhongliang ^b   Kerr, Russell G ^b,c   Davies, Huw M L ^a  

^a UNIVERSITY AT BUFFALO   (United States)

^b FLORIDA ATLANTIC UNIVERSITY   (United States)

^c UNIVERSITY OF PRINCE EDWARD ISLAND   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOHYDROQUINONE; ELISABETHAMINE; NATURAL PRODUCT;

AMINES; CHEMICAL ACTIVATION; CHEMICAL BONDS; MARINE ENGINEERING; OXIDATION; SYNTHESIS (CHEMICAL);

KETONES;

ELISABETHADIONE; ELISABETHAMINE; HYDROQUINONE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CORAL; NONHUMAN; PSEUDOPTEROGORGIA ELISABETHAE; STRUCTURE ANALYSIS; SYNTHESIS;

2-NAPHTHYLAMINE; ANIMALS; BENZOQUINONES; BIOLOGICAL PRODUCTS; HYDROQUINONES; MARINE BIOLOGY; METHYLATION; MOLECULAR STRUCTURE; NAPHTHOQUINONES; SEA URCHINS; SPECTRUM ANALYSIS; STEREOISOMERISM;

EID: 33947272690     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0618167     Document Type: Article

References (31)

1. For a general review on the isolation, synthesis, and biosynthesis of these natural products, see: Heckrodt, T. J.; Mulzer, J. Top. Curr. Chem. 2005, 244, 1-42.
2. Colombiasin A: (a) Isolation: Rodriguez, A. D.; Ramirez, C. Org. Lett. 2000, 2, 507-510.
3. Total synthesis: (b) Nicolaou, K. C.; Vassilikogiannakis, G.; Magerlein, W.; Kranich, R. Angew. Chem., Int. Ed. 2001, 40, 2482-2486.
4. (c) Nicolaou, K. C.; Vassilikogiannakis, G.; Magerlein, W.; Kranich, R. Chem. Eur. J. 2001, 7, 5359-5371.
5. (d) Kim, A. I.; Rychnovsky, S. D. Angew. Chem., Int. Ed. 2003, 42, 1267-1270.
6. (e) Harrowven, D. C.; Pascoe, D. D.; Demurtas, D.; Bourne, H. O. Angew. Chem., Int. Ed. 2005, 44, 1221-1222.
7. (f) Boezio, A. A.; Jarvo, E. R.; Lawrence, B. M.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44, 6046-6050.
8. For approaches toward colombiasin A: (a) Harrowven, D. C.; Tyte, M. J. Tetrahedron Lett. 2001, 42, 8709-8711.
9. (b) Chaplin, J, H.; Edwards, A. J.; Flynn, B. L. Org. Biomol. Chem. 2003, 1, 1842-1844.
10. Elisapterosin B: (a) Isolation: Rodriguez, A. D.; Ramirez, C.; Rodriguez, I. I.; Barnes, C. L. J. Org. Chem. 2000, 65, 1390-1398.
11. Total synthesis: (b) Waizumi, N.; Stankovic, A. R.; Rawal, V. H. J. Am. Chem. Soc. 2003, 125, 13022-13023. References 2d, 2e, and 2f.
12. Erogorgiaene: (a) Isolation: Rodriguez, A. D.; Ramirez, C. J. Nat. Prod. 2001, 64, 100-102.
13. Total synthesis: (b) Cesati, R. R.; Armas, J. D.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 96-101.
14. (c) Davies, H. M. L.; Walji, A. M. Angew. Chem., Int. Ed. Engl. 2005, 44 (11), 1733-1735.
15. Formal synthesis: (d) Harmata, M.; Hong, X. Tetrahedron Lett. 2005, 46, 3847-3849.
16. (a) Look, S. A.; Fenical, W.; Jacobs, R. S.; Clardy, J. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 6238-6240.
17. (b) Lazerwith, S. E.; Johnson, T. W.; Corey, E. J. Org. Lett. 2000, 2 (15), 2389-92.
18. (c) Corey, E. J.; Lazerwith, S. E. J. Am. Chem. Soc. 1998, 120, 12777-12782.
19. Ata, A.; Kerr, R. G.; Moya, C. E., Jacobs, R. S. Tetrahedron 2003, 59, 4215-4222.
20. Davies, H. M. L.; Dai, X.; Long, M. L. J. Am. Chem. Soc. 2006, 128, 2485-2490.
21. Davies, H. M. L.; Dai, X. Tetrahedron 2006, 62, 10477-10484.
22. Ata, A.; Kerr, R. G. Tetrahedron Lett. 2000, 41, 5821-5825.
23. (a) Carpino, L. A.; Triolo, S. A.; Berglund, R. A. J. Org. Chem. 1989, 54, 3303-3310.
24. (b) Watanabe, T.; Takeuchi, T.; Otsuka, M.; Umezawa, K. Chem. Commun. 1994, 4, 437.
25. (c) Harger, R. N. J. Am. Chem. Soc. 1924, 46, 2540.
26. (a) Fieser, L. F. J. Am. Chem. Soc. 1926, 48, 2922-2937.
27. (b) Fieser, L. F. J. Am. Chem. Soc. 1928, 50, 439-465.
28. (c) Cheng, H.; Cao, X.; Xian, M.; Fang, L.; Cai, T. B.; Ji, J. J.; Tunac, J. B.; Sun, D.; Wang, P. G. J. Med. Chem. 2005, 48, 645-652.
29. (a) Caldwell, W. T.; Thompson, T. R. J. Am. Chem. Soc. 1939, 61, 765-7.
30. (b) Sato, K.; Fujima, Yo.; Yamada, A. Bull. Chem. Soc. Jpn. 1968, 41, 442-4.
31. (c) Hegedus, L. S.; Mulhern, T. A.; Mori, A. J. Org. Chem. 1985, 50, 4282-4288.