Synthetic studies towards ciguatoxin via acetal/γ-oxovinyl stannane condensation: A convergent approach

Tetrahedron Letters

Volumn 37, Issue 16, 1996, Pages 2869-2872

  Ravelo, José Luis ^a   Regueiro, Alicia ^a   Rodríguez, Elsa ^a   De Vera, José ^a   Martín, Julio D ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DIOXANE DERIVATIVE; CIGUATOXIN; OXEPANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029868543     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00409-1     Document Type: Article

References (14)

1. Nicolaou, K.C. Aldrichimica Acta 1993, 26, 63.
2. Reviews: (a) Alvarez, A.; Candenas, M.-L.; Pérez, R.; Ravelo, J.L.; Martín, J.D. Chem. Rev. 1995, 95, 1953.
3. (b) Elliot, M.C. Contemp. Org. Synth. 1994, 1, 457.
4. For an overview, see: Yasumoto, T.; Murata, M. Chem. Rev. 1993, 93, 1897.
5. Alvarez, E.; Diaz, M.T.; Hanxing, L.; Martín , J.D. J. Am. Chem. Soc. 1995, 117, 1437.
6. Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361. Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448. Murata, M.; Legrand, A.M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380.
7. Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361. Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448. Murata, M.; Legrand, A.M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380.
8. Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361. Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448. Murata, M.; Legrand, A.M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380.
9. Satake, M.; Murata, M.; Yasumoto, T. Tetrahedron Lett. 1993, 34, 1975. Satake, M.; Murata, M.; Yasumoto, T. J. Am. Chem. Soc. 1993, 115, 361. Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448. Murata, M.; Legrand, A.M.; Ishibashi, Y.; Fukui, M.; Yasumoto, T. J. Am. Chem. Soc. 1990, 112, 4380.
10. For an excellent review of the history of ciguatoxin research, see: Scheuer, P.J. Tetrahedron 1994, 50, 1.
11. All new compounds exhibited satisfactory spectral and exact mass data. Yields have not been maximized and refer to spectroscopically and chromatographically homogeneous materials.
12. 3) δ 109.3 (s), 83.1 (d), 77.8 (d), 77.6 (d), 70.8 (d), 66.4 (t), 61.5 (t), 34.1 (t), 32.8 (t), 27.4 (t), 26.5 (q), 25.8 (q), 25.2 (q), 19.9 (s), -4.1 (q), -4.7 (q).
13. Alvarez, E.; Díaz, M.T.; Pérez, R.; Ravelo, J.L.; Regueiro, A.; de Vera, J.A.; Zurita, D.; Martín J.D. J. Org. Chem. 1994, 59, 2848.
14. 3) δ 170.8 (s), 170.1 (s), 138.1 (d), 138.0 (d), 114.8 (t), 114.6 (t), 84.2 (d), 84.2 (d), 83.6 (d), 83.6 (d), 77.3 (d), 75.3 (d), 74.3 (d), 71.6 (d), 71.3 (t), 70.7 (t), 64.0 (t), 60.8 (t), 31.3 (t), 31.2 (t), 31.2 (t), 29.9 (t), 29.7 (t), 28.9 (t), 26.6 (t), 21.1 (q), 21.0 (t), 21.0 (t), 21.0 (q).