The first construction of the B,C,D-ring fragment of pinnatoxins via highly stereocontrolled acetallization

Tetrahedron Letters

Volumn 38, Issue 42, 1997, Pages 7379-7382

  Sugimoto, Tetsuya ^a   Ishihara, Jun ^a   Murai, Akio ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

FISH VENOM; PINNATOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030796269     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01725-5     Document Type: Article

References (20)

1. Rosewater, J. Indo-Pac. Mollusca 1961, 1, 53/501.
2. (a) 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.
3. (b) Department of Public Health, Fukuoka Prefecture. Food Sanit. Res. 1976, 26, 11.
4. Zeng, S. Z.; Huang, F, L.; Chen, S. C.; Tan, X. F.; Zuo, J. B.; Peng, J.; Xie, R. W. Zhongguo Haiyang Yaowu (Chinese J. of Marine Drugs) 1990, 33, 33.
5. (a) Uemura, D.; Chou, T.; Haino, T.; Nagatsu, A; Fukuzawa, S.; Zeng, S. Z.; Chen, H. S. J. Am. Chem. Soc. 1995, 117, 1155.
6. (b) Chou, T.; Kamo, O.; Uemura, D. Tetrahedron Lett. 1996, 37, 4023.
7. (c) Chou, T.; Haino, T.; Kuramoto, M.; Uemura, D. Tetrahedron Lett. 1996, 37, 4027.
8. (a) Perron, F.; Albizati, K. F. J. Org. Chem., 1989, 54, 2044.
9. (b) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: New York, 1983.
10. Oka, T.; Murai, A. Chem. Lett. 1994, 1611.
11. (a) Ravid, U.; Silverstein, R. M.; Smith, L. R. Tetrahedron, 1978, 34, 1449.
12. (b) Cole, A. G.; Wilkie, J.; Gani, D. J. Chem. Soc. Perkin Trans. 1, 1995, 2695.
13. (c) Herdeis, C. Synthesis, 1986, 232.
14. (d) Brunner, H.; Lautenshlager, H. J. Synthesis, 1989, 706.
15. (e) Hartman, F. C.; Barker, R. J. Org. Chem., 1964, 29, 873.
16. (a) Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem., 1981, 46, 3936.
17. (b) Zibuck, R.; Seebach, D. Helv. Chim. Acta, 1988, 71, 237.
18. (c) Gopal, H.; Gordon, A. J. Tetrahedron Lett., 1971, 2941.
19. (d) Carling, R. W.; Holmes, A. B. Tetrahedron Lett., 1986, 27, 6133.
20. -1.