Synthesis of symmetric HIJ-ring model of ciguatoxin

Tetrahedron

Volumn 63, Issue 26, 2007, Pages 5886-5894

  Nonoyama, Akihito ^a   Hamajima, Akinari ^a   Isobe, Minoru ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CIGUATOXIN; OXOCIN DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; DIASTEREOISOMER; ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 34248684098     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.012     Document Type: Article

References (28)

1. Nakata T. Chem. Rev. 105 (2005) 4314-4347
2. Isolation:. Scheuer P.J., Takahashi W., Tsutumi J., and Yoshida T. Science 155 (1967) 1267-1268 Structure:
3. Murata M., Legurand A.M., Ishibashi Y., Fukui M., and Yasumoto T. J. Am. Chem. Soc. 112 (1990) 4380-4386
4. Satake M., Morohashi A., Oguri H., Oishi T., Hirama M., Harada N., and Yasumoto T. J. Am. Chem. Soc. 119 (1997) 11325-11326
5. Yasumoto T. Chem. Rec. 1 (2001) 228-242 Total synthesis:
6. Hirama M., Oishi T., Uehara H., Inoue M., Maruyama M., Oguri H., and Satake M. Science 294 (2001) 1904-1907
7. Inoue M., Miyazaki K., Ishihara Y., Tatami A., Ohuma Y., Komano K., Yamashita S., Lee N., and Hirama M. J. Am. Chem. Soc. 128 (2006) 9352-9354
8. Isobe M., Yenjai C., and Tanaka S. Synlett (1994) 916-918
9. Yenjai C., and Isobe M. Tetrahedron 54 (1998) 2509-2520
10. Isobe M., Hosokawa S., and Kira K. Chem. Lett. (1996) 473-474
11. Hosokawa S., and Isobe M. J. Org. Chem. 64 (1999) 37-48
12. Saeeng R., and Isobe M. Tetrahedron Lett. 40 (1999) 1911-1914 For a review, see Ref. 7a
13. Hamajima A., and Isobe M. Org. Lett. 8 (2006) 1205-1208
14. Nicolaou K.C., Hwang C.-K., Marron B.E., De Frees S.A., Couladouros E.A., Abe Y., and Caroll P.J. J. Am. Chem. Soc. 112 (1990) 3040-3054
15. Fujiwara K., Morishita H., Saka K., and Murai A. Tetrahedron Lett. 41 (2000) 507-508
16. Hara S., Dojo H., Takinami S., and Suzuki A. Tetrahedron Lett. 24 (1983) 731-734
17. Isobe M., Nishizawa R., Hosokawa S., and Nishikawa T. Chem. Commun. (1998) 2665-2676
18. Shibuya S., and Isobe M. Tetrahedron 54 (1998) 6677-6698
19. Takai S., Ploypradith P., Hamajima A., Kira K., and Isobe M. Synlett (2002) 588-592
20. Hosokawa S., and Isobe M. Tetrahedron Lett. 39 (1998) 2609-2612
21. Kira K., Tanda H., Hamajima A., Baba T., Takai S., and Isobe M. Tetrahedron 58 (2002) 6485-6492
22. It was calculated which dihedral angle of C{double bond, long}O and C{double bond, long}C was fixed on the same plane as transition state.
23. Scheiper B., Bonnekessel M., Krause H., and Fürstner A. J. Org. Chem. 69 (2004) 3943-3949
24. Crabtree R.H., and Morris G.E. J. Chem. Soc., Chem. Commun. (1976) 716-717
25. Domon D., Fujiwara K., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 46 (2005) 8285-8288
26. Liu T.-Z., Li J.-M., and Isobe M. Tetrahedron 56 (2000) 10209-10219
27. Shida, T.; Tachibana, K. 46th Symposium on The Chemistry of Natural Products, Hiroshima, 2004; pp 227-231.
28. Takai S., Sawada N., and Isobe M. J. Org. Chem. 68 (2003) 3225-3231