A synthesis of (+)-saxitoxin

Journal of the American Chemical Society

Volumn 128, Issue 12, 2006, Pages 3926-3927

  Fleming, James J ^a   Du Bois, J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

SAXITOXIN; SODIUM CHANNEL;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DEPROTECTION REACTION; STEREOCHEMISTRY; STEREOISOMERISM; TOXIN SYNTHESIS;

SAXITOXIN; STEREOISOMERISM;

EID: 33645460680     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0608545     Document Type: Article

References (29)

1. (a) Lehane, L. Paralytic Shellfish Poisoning: A Review. National Office of Animal and Plant Health, Agriculture, Fisheries and Forestry, Canberra, Australia, 2000.
2. (b) Kao, C. Y.; Levinson, S. R. Tetrodotoxin, Saxitoxin, and the Molecular Biology of the Sodium Channel; New York Academy of Sciences: New York, 1986.
3. Schantz, E. J.; Mold, J. D.; Stanger, D. W.; Shavel, J.; Riel, F. J.; Bowden, J. P.; Lynch, J. M.; Wyler, R. S.; Riegel, B.; Sommer, H. J. Am. Chem. Soc. 1957, 79, 5230-5235.
4. (a) Schantz, E. J.; Ghazarossian, V. E.; Schnoes, H. K.; Strong, F. M.; Springer, J. P.; Pezzanite, J. O.; Clardy, J. J. Am. Chem. Soc. 1975, 97, 1238-1239.
5. (b) Bordner, J.; Thiessen, W. E.; Bates, H. A.; Rapoport, H. J. Am. Chem. Soc. 1975, 97, 6008-6012.
6. (a) Tanino, H.; Nakata, T.; Kaneko, T.; Kishi, Y. J. Am. Chem. Soc. 1977, 99, 2818-2819.
7. (b) Kishi, Y. Heterocycles 1980, 14, 1477-1495.
8. (a) Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Am. Chem. Soc. 1984, 106, 5594-5598.
9. (b) Martinelli, M. J.; Brownstein, A. D.; Jacobi, P. A.; Polanc, S. Croat. Chem. Acta 1986, 59, 267-295.
10. Hille, B. Ion Channels of Excitable Membranes, 3rd ed.; Sinauer: Sunderland, MA, 2001.
11. (a) Strichartz, G. R.; Hall, S.; Magnani, B.; Hong, C. Y.; Kishi, Y.; Debin, J. A. Toxicon 1995, 33, 723-737.
12. (b) Tikhonov, D. B.; Zhorov, B. S. Biophys. J. 2005, 88, 184-197.
13. (c) Choudhary, G.; Shang, L.; Li, X.; Dudley, S. C. Biophys. J. 2002, 83, 912-919.
14. Shimizu, Y.; Hsu, C. P.; Genenah, A. J. Am. Chem. Soc. 1981, 103, 605-609.
15. For an example of α-ketol formation followed by transannular cyclization, see: Vedejs, E.; Galante, R. J.; Goekjian, P. G. J. Am. Chem. Soc. 1998, 120, 3613-3622.
16. Fleming, J. J.; Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 2028-2029.
17. (R)-Glycerol acetonide was purchased from Oakwood Products, Inc.
18. Analogous reagents have been described for guanidine synthesis. See: Bosin, T. R.; Hanson, R. N.; Rodricks, J. V.; Simpson, R. A.; Rapoport, H. J. Org. Chem. 1973, 38, 1591-1600.
19. Merchán, F. L.; Garín, J.; Tejero, T. Synthesis 1982, 984-986.
20. Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
21. Fukada, N.; Takano, M.; Nakai, K.; Kuboike, S.; Takeda, Y. Bull. Chem. Soc. Jpn. 1993, 66, 148-152.
22. Kočovský, P. Tetrahedron Lett. 1986, 5521-5524.
23. (a) Plietker, B. J. Org. Chem. 2004, 69, 8287-8296.
24. (b) Murahashi, S. I.; Naota, T.; Hanaoka, H. Chem. Lett. 1993, 1767-1770.
25. (c) Miescher, K.; Schmidlin, J. U.S. Patent 2,668,816, 1954.
26. Pless, J.; Bauer, W. Angew. Chem., Int. Ed. Engl. 1973, 12, 147-148.
27. Koehn, F. E.; Ghazarossian, V. E.; Schantz, E. J.; Schnoes, H. K.; Strong, F. M. Bioorg. Chem. 1981, 10, 412-428.
28. Negri, A.; Stirling, D.; Quilliam, M.: Blackburn, S.; Bolch, C.; Burton, I.; Eaglesham, G.; Thomas, K.; Walter, J.; Willis, R. Chem. Res. Toxicol. 2003, 16, 1029-1033.
29. Moran, O.; Picollo, A.; Conti, F. Biophys. J. 2003, 84, 2999-3006.