Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, methoxy-(2-naphthyl)acetic acid

Tetrahedron Letters

Volumn 37, Issue 39, 1996, Pages 7087-7090

  Takahashi, Haruko ^a   Kusumi, Takenori ^a   Kan, Yukiko ^b   Satake, Masayuki ^c   Yasumoto, Takeshi ^c  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

MARINE TOXIN; UNCLASSIFIED DRUG; YESSOTOXIN;

ARTICLE; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE;

EID: 0030599253     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01580-8     Document Type: Article

References (16)

1. 1. Yasumoto, T.; Murata, M. Chem. Rev., 1993, 93, 1897-1909.
2. 2. (a) Lin, Y. -Y.; Risk, M.; Ray, S. M.; Van Engen, D.; Clardy, J.; Golik, J.; James, J. C.; Nakanishi, K. J. Am. Chem. Soc., 1981, 103, 6773-6775.
3. (b) Very recently, the absolute configuration of mitotoxin has been elucidated: (i) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl., 1996, in press, (ii) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl., 1996, in press.
4. (b) Very recently, the absolute configuration of mitotoxin has been elucidated: (i) Sasaki, M.; Matsumori, N.; Maruyama, T.; Nonomura, T.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl., 1996, in press, (ii) Nonomura, T.; Sasaki, M.; Matsumori, N.; Murata, M.; Tachibana, K.; Yasumoto, T. Angew. Chem., Int. Ed. Engl., 1996, in press.
5. 3. (a) Murata, M.; Kumagai, M.; Lee, J. S.; Yasumoto, T. Tetrahedron Lett., 1987, 28, 5869-5872.
6. (b) Satake, M.; Terasawa, K.; Kadowaki, Y.; Yasumoto, T. Tetrahedron Lett., 1996, in press.
7. 4. (a) Kusumi, T.; Takahashi, H.; Ping, X.; Fukushima, T.; Asakawa, Y.; Hashimoto, T.; Kan, Y.; Inouye, Y. Tetrahedron Lett., 1994, 35, 4397-4400.
8. (b) Kusumi, T.; Takahashi, H.; Hashimoto, T.; Kan, Y.; Asakawa, Y. Chemistry Lett., 1994, 1093-1094.
9. 5. (a) Seco, J. M.; Latypov, Sh. K.; Quinoa, E.; Riguera, R. Tetrahedron Lett., 1994, 35, 2921-2924.
10. (b) Latypov, Sh. K.; Seco, J. M.; Quinoa, E.; Riguera, R. J. Org. Chem., 1995, 60, 504-515.
11. 6. Kouda, K.; Kusumi, T.; Kan, Y.; Hashimoto, T.; Asakawa, Y. Tetrahedron Lett., 1996, 37, 4541-4544.
12. 7. Nagai, Y.; Kusumi, T. Tetrahedron Lett., 1995, 36, 1853-1856.
13. 8. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc., 1991, 113, 4092-4096.
14. 9. (R)-and (S)-2NMA are available on request. (E-mail: tkusumi@ph.tokushima-u.ac. jp).
15. 2 = Ac). This minor product could be eliminated by HPLC after conversion into 2NMA esters.
16. 11. Kimura, T.; Takai, M.; Masui, Y.; Morikawa, T.; Sakakibara, S. Biopolymers, 1981, 20, 1823-1826.