The absolute stereochemistry of the New Zealand shellfish toxin gymnodimine

Tetrahedron Letters

Volumn 38, Issue 27, 1997, Pages 4889-4890

  Stewart, Michael ^a   Blunt, John W ^a   Munro, Murray H G ^a   Robinson, Ward T ^a   Hannah, Donald J ^b  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b INSTITUTE OF ENVIRONMENTAL SCIENCE AND RESEARCH   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

MARINE TOXIN;

ARTICLE; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SHELLFISH; STEREOCHEMISTRY; TOXIN ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0030958798     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01050-2     Document Type: Article

References (10)

1. Mackenzie, L. Seafood New Zealand 1994, 2, 47-50.
2. Seki, T.; Satake, M.; Mackenzie, L.; Kaspar, H.F.; Yasumoto, T. Tetrahedron Lett. 1995, 36, 7093-7096.
3. Chou, T.; Haino, T.; Kuramoto, M.; Uemura, D. Tetrahedron Lett. 1996 37, 4027-4030, and references cited therein.
4. Hu, T.; Curtis, J.M.; Oshima, Y.; Quilliam, M.A.; Walter, J.A.; Watson-Wright, W.M.; Wright, J.L.C. J. Chem. Soc. Chem. Commun. 1995, 2159-2161. Hu, T.; Curtis, J.M.; Walter, J.A.; Wright, J.L.C. Tetrahedron Lett. 1996, 37, 7671-7674.
5. Hu, T.; Curtis, J.M.; Oshima, Y.; Quilliam, M.A.; Walter, J.A.; Watson-Wright, W.M.; Wright, J.L.C. J. Chem. Soc. Chem. Commun. 1995, 2159-2161. Hu, T.; Curtis, J.M.; Walter, J.A.; Wright, J.L.C. Tetrahedron Lett. 1996, 37, 7671-7674.
6. Minimum Lethal Doses (MLD) (intraperitoneal): gymnodamine 2, >4040 μg/kg; gymnodimine 1, 700 μg/kg.
7. 2:pet. ether and on AMINO with MeOH to afford gymnodimine 1 (8.4 mg).
8. + m/z 509.3495 Δ-2.01 ppm). All spectral data were consistent with 2.
9. 3) (major conformation) 7.52, d, J = 8.8, 2H, H4′ H6′ 7.19, d, J = 8.3, 2H, H3′ H7′; 6.88, bs, 1H, H3; 5.72, bs, 1H, H4; 5.38, t, J = 6.3, 7.8, 1H, H18; 5.20, d, J= 10.7, 1H, H8; 4.50, dd, J = 3.4, 8.8, 2.9, 1H, H21; 4.15, m, 1H, H13; 3.94, obs, 1H, H10; 3.92, bs, 1H, H16; 3.46, dd, J = 5.4, 10.3, 1.4, 1H, H32a; 2.99, d, J = 11.2, 1H, H7; 2.95, obs, H32b; 2.48, m, 1H, H15; 2.15, m, H19; 2.00, obs, H11a; 1.94, s, 3H, Me25; 1.77, s, 3H, Me27; 1.67, s, 3H, Me29; 1.60, s, 3H, Me26; 1.08, d, J = 7.3, 3H, Me28.
10. 1 for inverse stucture = 0.0574.