Relative stereochemistry of pinnatoxin A, a potent shellfish poison from Pinna muricata

Tetrahedron Letters

Volumn 37, Issue 23, 1996, Pages 4023-4026

  Chou, Tong ^c   Kamo, Osamu ^a   Uemura, Daisuke ^b  

^a JEOL LTD   (Japan)

^b SHIZUOKA UNIVERSITY   (Japan)

^c SAGAMI CHEMICAL RESEARCH CENTER   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FISH VENOM; PINNATOXIN A; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

PINNA MURICATA;

EID: 0029943184     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00752-6     Document Type: Article

References (12)

1. Otofuji, T.; Ogo, A.; Koishi, J.; Matsuo, K.; Tokiwa, H.; Yasumoto, T.; Nishihara, K.; Yamamoto, E.; Saisho, M.; Kurihara, Y.; Hayashida, K. Food Sanit. Res. 1981, 31, 76-83.
2. Department of Public Health, Fukuoka Prefecture, Food Sanit. Res. 1976, 26, 11-20.
3. Zheng, S. Z.; Huang, F. L.; Chen, S. C.; Tan, X. F.; Zuo, J. B.; Peng, J.; Xie, R. W. Zhongguo HaiyangYaowu (Chinese J. of Marine Drugs). 1990, 33, 33-35.
4. Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A.; Fukuzawa, S.; Zheng, S. Z.; Chen, H. S. J. Am. Chem. Soc. 1995, 117, 1155.
5. 3OD, with a mixing time of 250 ms .
6. NOESY: Kumar, A.; Ernst, R. R.; Wuthrich, K., Biochem. Biophys. Res. Commun., 1980, 95, 1.
7. ROESY: Bax, A.; Davis, D. G.; J. Magn. Reson., 1985, 63, 207.
8. 3JH1-H6a =0 Hz were also reported: Brügel, W. HandBook of NMR Spectral Parameters; Vol. 1, Heyden & Son, Ltd.: London, Philadelphia, 1979; pp. 104-117.
9. 6 with mixing times of 400 ms. NOEs correlations were observed through the crosspeaks H32/H29, H32/H28, H32/H31, H31/H27, H31/H7, H30/H4b and H28/-OMe.
10. Eliel, E. L. Stereochemistry of Carbon Compounds; McGraw-Hill Book Company, Inc.: New York, San Francisco, Toront, London, 1962; pp. 252-253.
11. (a) Anders, L. R.; Baldeschwieler, J. D.; J. Chem. Phys., 1965, 43, 2147.
12. (b) Afanas'ev, V. A.; Bystrov, V. F.; J. Magn. Reson., 1970, 3, 357.