Further studies on the chemistry of the flustra alkaloids from the bryozoan Flustra foliacea

Journal of Natural Products

Volumn 72, Issue 10, 2009, Pages 1773-1781

  Rochfort, Simone J ^a,c   Moore, Stanley ^a,d   Craft, Cheryl ^a   Martin, Ned H ^b   Van Wagoner, Ryan M ^b   Wright, Jeffrey L C ^a,b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

^c DEPARTMENT OF PRIMARY INDUSTRIES   (Australia)

^d UNIVERSITY OF SASKATCHEWAN   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID DERIVATIVE; DEBROMOFLUSTRAMINE H; DIHYDROFLUSTRAMINE C; FLUSTRAMINE F; FLUSTRAMINE G; FLUSTRAMINE H; FLUSTRAMINE I; FLUSTRAMINE J; FLUSTRAMINE K; FLUSTRAMINE L; FLUSTRAMINE M; FLUSTRAMINE N; FLUSTRAMINE O; FLUSTRAMINE P; PERMETHYLFLUSTRAMINE H; UNCLASSIFIED DRUG;

ARTICLE; BRYOZOA; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG ISOLATION; DRUG STRUCTURE; FLUSTRA FOLIACEA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE;

ALKALOIDS; ANIMALS; BRYOZOA; HYDROCARBONS, BROMINATED; MARINE BIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR;

BRYOZOA; FLUSTRA; FLUSTRA FOLIACEA; GYMNOLAEMATA;

EID: 70350512836     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np900282j     Document Type: Article

References (30)

1. Pettit, G. R.; Herald, C. L.; Doubek, D. L.; Herald, D. L.; Arnold, E.; Clardy, J. J. Am. Chem. Soc. 1982, 104, 6846-6848.
2. Carlé, J. S.; Christophersen, C. J. Am. Chem. Soc. 1979, 101, 4012-4013.
3. Carlé, J. S.; Christophersen, C. J. Org. Chem. 1980, 45, 1586-1589.
4. Carlé, J. S.; Christophersen, C. J. Org. Chem. 1981, 46, 3440-3443.
5. Wright, J. L. C. J. Nat. Prod. 1984, 47, 893-895.
6. Laycock, M. V.; Wright, J. L. C.; Findlay, J. A.; Patil, A. D. Can. J. Chem. 1986, 64, 1312-1316.
7. Holst, P. B.; Anthoni, U.; Christophersen, C.; Nielsen, P. H. J. Nat. Prod. 1994, 57, 997-1000.
8. Keil, P.; Nielsen, E. G.; Anthoni, U.; Christophersen, C. Acta Chem. Scand. B 1986, B40, 555-558.
9. Holst, P. B.; Anthoni, U.; Christophersen, C.; Nielsen, P. H. J. Nat. Prod. 1994, 57, 1310-1312.
10. Wulff, P.; Carlé, J. S.; Christophersen, C. Comp. Chem. Physiol., B: Biochem. Mol. Biol. 1982, 71, 523-524.
11. Sjöblom, T.; Bohlin, L.; Christophersen, C. Acta Pharm. Suecica 1983, 20, 415-418.
12. Peters, L.; König, G. M.; Terlau, H.; Wright, A. D. J. Nat. Prod. 2002, 65, 1633-1637.
13. Peters, L.; Wright, A. D.; Kehraus, S.; Gündisch, D.; Tilotta, M. C.; König, G. M. Planta Med. 2004, 70, 883-886.
14. Hino, T.; Tanaka, T.; Matsuki, K.; Nakagawa, M. Chem. Pharm. Bull. 1983, 31, 1806-1808.
15. Muthusubramanian, P.; Carlé, J. S.; Christophersen, C. Acta Chem. Scand. B 1983, B37, 803-807.
16. Bruncko, M.; Crich, D.; Samy, R. J. Org. Chem. 1994, 59, 5543-5549.
17. Austin, J. F.; Kim, S.-G.; Sinz, C. J.; Xiao, W.-J.; MacMillan, D. W. C. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5482-5487.
18. Takase, S.; Uchida, I.; Tanaka, H.; Aoki, H. Heterocycles 1984, 22, 2491-2494.
19. Takase, S.; Uchida, I.; Tanaka, H.; Aoki, H. Tetrahedron 1986, 42, 5879-5886.
20. Kawasaki, T.; Terashima, R.; Sakaguchi, K.; Sekiguchi, H.; Sakamoto, M. Tetrahedron Lett. 1996, 37, 7525-7528.
21. Morales-Ríos, M. S.; Suárez-Castillo, O. R.; Trujillo-Serrato, J. J.; Joseph-Nathan, P. J. Org. Chem. 2001, 66, 1186-1192.
22. Morales-Ríos, M. S.; Suárez-Castillo, O. R.; Joseph-Nathan, P. Tetrahedron 2002, 58, 1479-1484.
23. Fuchs, J. R. New Strategies for the Synthesis of Polycyclic Natural Products: Total Syntheses of Lennoxamine, Aphanorphine, Flustramine A, Flustramine C, and Perophoramidine. Ph.D. Thesis, Pennsylvania State University, University Park, PA, 2005.
24. Kawasaki, T.; Shinada, M.; Kamimura, D.; Ohzono, M.; Ogawa, A. J. Chem. Soc., Chem. Commun. 2006, 420-422.
25. Crews, P.; Farias, J. J.; Emrich, R.; Keifer, P. A. J. Org. Chem. 1994, 59, 2932-2934.
26. Sadtler Research Laboratories, I. 1975; pp 1290C and 21266.
27. Sato, A.; Fenical, W. Tetrahedron Lett. 1983, 24, 481-484.
28. Sykes, P. A Guidebook to Mechanism in Organic Chemistry, 6th ed.; Longman Group Ltf: Essex, 1986.
29. Nickon, A.; Weglein, R. C. J. Am. Chem. Soc. 1975, 97, 1271-1273.
30. Sculpt modeling program; HyperCube, Inc., 1995.