Structures and absolute configurations of the marine toxins, latrunculin A and laulimalide

Tetrahedron Letters

Volumn 37, Issue 2, 1996, Pages 159-162

  Jefford, Charles W ^a   Bernardinelli, Gérald ^a   Tanaka, Jun Ichi ^b   Higa, Tatsuo ^b  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b UNIVERSITY OF THE RYUKYUS   (Japan)

Author keywords

2 thiazolidinone; dihydropyran; fijianolide; macrolide; X ray

Indexed keywords

LATRUNCULIN A; LAULIMALIDE; MARINE TOXIN; UNCLASSIFIED DRUG;

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

FASCIOSPONGIA;

EID: 0030068561     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02113-2     Document Type: Article

References (15)

1. P.M. Blumberg and G.R. Pettit, "The Bryostatins, a family of protein kinase C activators with therapeutic potential", in New Leads and Targets in Drug Research. Alfred Benzon Symposium 33 (P. Krogsgaard-Larsen, S. Brogger Christensen, and H. Kofod, eds.). Munksgaard, Copenhagen, 1992, pp 273-285; C. Stanwell, A. Gescher, T.D. Bradshaw and G.R. Pettit, Int. J. Cancer 1994, 56, 585-592.
2. P.M. Blumberg and G.R. Pettit, "The Bryostatins, a family of protein kinase C activators with therapeutic potential", in New Leads and Targets in Drug Research. Alfred Benzon Symposium 33 (P. Krogsgaard-Larsen, S. Brogger Christensen, and H. Kofod, eds.). Munksgaard, Copenhagen, 1992, pp 273-285; C. Stanwell, A. Gescher, T.D. Bradshaw and G.R. Pettit, Int. J. Cancer 1994, 56, 585-592.
3. For details of miyakolide, a bryostatin-like macrolide, see: T. Higa, J. Tanaka, M. Komesu, D. García Gravalos, J.L. Fernández Puentes, G. Bernardinelli, and C.W. Jefford, J. Am. Chem. Soc. 1992, 114, 7587-7588.
4. Y. Kashman, A. Groweiss, and U. Shmueli, Tetrahedron Lett. 1980, 21, 3629-3632; A. Groweiss, U. Shmueli, and Y. Kashman, J. Org. Chem. 1983, 48, 3512-3516.
5. Y. Kashman, A. Groweiss, and U. Shmueli, Tetrahedron Lett. 1980, 21, 3629-3632; A. Groweiss, U. Shmueli, and Y. Kashman, J. Org. Chem. 1983, 48, 3512-3516.
6. E. Quiñoà, Y. Kakou, and P. Crews, J. Org. Chem. 1988, 53, 3642-3644.
7. D.G. Corley, R. Herb, R.E. Moore, P.J. Scheuer, and V.J. Paul, J. Org. Chem. 1988, 53, 3644-3646.
8. N.K. Gulavita, S.P. Gunasekera, and S.A. Pomponi, J. Nat. Prod. 1992, 55, 506-508. A note added in proof suggested that all three sponges belong to the same species.
9. I. Spector, N.R. Shochet, Y. Kashman, and A. Groweiss, Science 1983, 219, 493-495.
10. Y. Kashman, A. Groweiss, R. Lidor, D. Blasberger, and S. Carmely, Tetrahedron 1985, 41, 1905-1914.
11. Taxonomic identification was performed by Dr. J.N.A. Hooper, Queensland Museum, Brisbane, Qld., Australia. A voucher specimen (No. G301467) has been deposited at the museum.
12. 3): δ 20.7 (C30), 22.9 (C28), 29.5 (C11), 31.6 (C8), 33.3 (C18), 33.8 (C4), 35.6 (C24), 37.1 (C14), 43.4 (C10), 45.5 (C12), 52.1 (17), 60.7 (C16), 65.6 (C27), 66.5 (C15), 67.9 (C9), 72.3 (C19), 73.1 (C5), 73.2 (C20), 73.4 (C23), 112.5 (C29), 119.7 (C26), 120.5 (C2), 125.2 (C7), 128.5 (C6), 128.7 (C21) , 131.2 (C25), 133.8 (C22), 144.9 (C13), 150.3 (C3), 166.0 (C1).
13. 2(Fo)) for 37861 observed reflections (|Fo| > 4σ(Fo)). Crystallographic data have been deposited with the Cambridge Crystallographic Data Center, University Chemical Laboratory, 12 Union Road, Cambridge CB2 1EZ, England.
14. M. Nardelli, Acta Cryst. 1983, C39, 1141-1142.
15. G. Bernardinelli and H.D. Flack, Acta Cryst. 1985, A41, 500-511.