The structure and biogenetic origin of (-) halicyclamine B from a Xestospongia sponge

Tetrahedron Letters

Volumn 37, Issue 51, 1996, Pages 9151-9154

  Harrison, Blaine ^a   Talapatra, Sunil ^a   Lobkovsky, Emil ^b   Clardy, Jon ^b   Crews, Phillip ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SPONGE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

XESTOSPONGIA;

EID: 0030590950     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02165-X     Document Type: Article

References (22)

1. 1. Baldwin, J.E.; Claridge, T.D.W.; Heupel, F.A.; Whitehead, R.C. Tetrahedron Lett. 1994, 35, 7829-7832.
2. 2. (a) Sakai, R.; Higa, T. J. Am. Chem. Soc. 1986, 108, 6404-6405.
3. (b) Nakamura, H.; Deng, S.; Kobayashi, J.; Ohizumi, Y.; Tomotake, Y.; Matsuzaki, T.; Hirata, Y. Tetrahedron Lett. 1987, 28, 621-624.
4. (c) Sakai, R.; Kohmoto, S.; Higa, T.; Jefford, C.; Bernardinelli, G. Tetrahedron Lett. 1987, 28, 5493-5496.
5. 3. Ohtani, I.I.; Ichiba, T.; Isobe, M.; Kelly-Borges, M.; Scheuer, P.J. J. Am. Chem. Soc. 1995, 117, 10743-10744.
6. 4. (a) Baker, B.J.; Scheuer, P.J; Shoolery, J.N. J. Am. Chem. Soc. 1988, 110, 965-966.
7. (b) Fahy, E.; Molinski, T.F.; Harper, M.K.; Sullivan, B.W.; Faulkner, D.J. Tetrahedron Lett. 1988, 29, 3427-3428.
8. (c) Barrett, A.G.M.; Boys, M. L.; Boehm, T. L. J. Org. Chem. 1996, 61, 685-699.
9. 5. Kondo, K.; Shigemori, H.; Kikuchi, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1992, 57, 2480-2483.
10. 6. (a) Rodríguez, J.; Crews, P. Tetrahedron Lett. 1994, 35, 4719-4722.
11. (b) Kong, F.; Anderson, R. Tetrahedron 1995, 51, 2895-2906.
12. (c) Tsuda, M.; Inaba, K.; Kawasaki, N.; Honma, K.; Kobayashi, J. Tetrahedron 1996, 52, 2319-2324.
13. (d) Kong, F.; Anderson, R.J. Tetrahedron 1994, 50, 6137-6144.
14. 7. (a) Jaspers, M.; Pasupathy, V.; Crews, P. J. Org. Chem. 1994, 59, 3253-3255.
15. (b) Charan, R. D.; Garson, M. J.; Brereton, I. M.; Willis, A. C.; Hooper, J. N. A. Tetrahedron 1996, 52, 9111-9120.
16. o). Coordinates have been deposited.
17. 9. Valeriote, F.; Corbett, T.; LoRusso, P.; Moore, R.E.; Scheuer, P.J; Patterson, G.; Paul, V.; Grindey, G.; Bonjouklian, R.; Pearce, H.; Suffness, M. I. J. Pharmacognosy 1995, 33, Supplement 59-66.
18. 10. Gil, L.; Baucherel, X.; Martin, M.T.; Marazano, C.; Das, B.C. Tetrahedron Lett. 1995, 36, 6231-6234, and refs within.
19. 11. (a) The αH1′ and αC26′ stereochemistry shown in Scheme 1 has been implied for the following: (+) manzamine J: Ref. 6c; 6-hydroxymanzamine A and (+) 3,4,-dihydromanzamine A: Kobayashi, J.; Tsuda, M.; Kawasaki, N. J. Nat. Prod. 1994, 57, 1737-1740.
20. 6a
21. 6b does not appear to fit this preceeding relationship.
22. 12. Tsuda, M.; Kawasaki, N.; Kobayashi, J. Tetrahedron, 1994, 50, 7957-7960.