Ortho-condensed oxane/polyoxygenated macrorings by ruthenium-catalyzed ring closing metathesis

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8387-8390

  Delgado, Mercedes ^a   Martín, Julio D ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; MACROCYCLIC COMPOUND; POLYETHER; POLYOL;

ALKYLATION; ARTICLE; CYCLIZATION; ION TRANSPORT; OXYGENATION; POLYMERIZATION; SYNTHESIS;

EID: 0030719482     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10173-3     Document Type: Article

References (27)

1. Nichols, D.G. Proteins, Transmitters and Synapses; Blackwell Science: Oxford, U.K., 1994.
2. (a) Betz, H. Biochemistry 1990, 29, 3591-3599.
3. (b) Stroud, R.M.; McCarthy, M.P.; Shuster, M. Biochemistry 1990, 29, 11009-11023.
4. (a) Langs, D.A. Science 1988, 241, 188-191.
5. (b) Wallace, B.A.; Kavikumar, K. Science 1988, 241, 182-187.
6. (c) Urry, E.W.; Goodall, M.C.; Grickson, J.D.; Meyers, D.F. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 1907-1910.
7. (d) Urruy, D.W. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 672-676.
8. (a) Bolard, J.; Legrand, P.; Heitz, F.; Cybulska, B. Biochemistry 1991, 30, 5707-5715.
9. (b) Harstel, S.C.; Perkins, W.R.; McGarvey, G.J.; Cafiso, D.S. Biochemistry 1988, 27, 2656-2660.
10. (c) Bolard, J. Biochim. Biophys. Acta. 1986, 864, 257-304.
11. For recent reviews related with synthetic models for transmembrane channels, see: (a) Gokel, G.W.; Murillo, O. Acc. Chem. Res. 1996, 29, 425-432.
12. (b) Akerfeldt, K.S.; Lear, J.D.; Wasserman, Z.R.; Chung, L.A.; DeGrado, W.F. Acc. Chem. Res. 1993, 26, 191-197.
13. Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S.L. J. Am. Chem. Soc. 1994, 116, 6677-6682.
14. Recent findings showing that substituted crown ethers can serve as head groups for the formation of stable vesicles comports with this design: (a) Muñoz, S.; Mallén, J.V.; Nakano, A.; Chen, Z.; Gay, L; Echegoyen, L.; Gokel, G.W. J. Chem. Soc. Chem. Commun. 1992, 520-522.
15. (b) Muñoz, S.; Mallén, J. V.; Nakano, A.; Chen, Z.; Gay, L; Echegoyen, L; Gokel, G.W. J. Am. Chem. Soc. 1993, 115, 1705-1711.
16. (c) Murillo, O.; Suzuki, L; Abel, E.; Murray, C.L.; Meadows, E.S.; Jin, T.; Gokel, G.W. J. Am. Chem. Soc. 1997, 119, 5540-5549.
17. (d) Abel, E.; Meadows, E.S., Suzuki, I.; Jin, T.; Gokel, G.W. J. Chem. Soc. Chem. Commun. 1997, 1145-1146.
18. Transmembrane self-assembly of the natural trans-fused polyether brevetoxin-B and selective cation transport across lipid bilayers via a channel-like mechanism has been recently reported: (a) Matile, S.; Berova, N.; Nakanishi, K. Chemistry Biology 1996, 3, 379-392.
19. (b) Matile, S.; Nakanishi, K. Angew. Chem. Int. Ed. Engl. 1996, 35, 757-759.
20. The potency of antifungal activity of gambieric acids, natural polar-ended trans-fused polyethers, exceeds that of AmpB 2000-fold: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. As occurs with AmpB, the higher sensitivity of fungal cells to gambieric acids action, probably originates from its higher affinity for ergosterol-containing membranes (fungal cells) as compared to cholesterol-containing membranes (mammalian cells): Bolar, J.; Legrand, P.; Heitz, F.; Cybulska, B. Biochemistry 1991, 30, 5707-5715.
21. The potency of antifungal activity of gambieric acids, natural polar-ended trans-fused polyethers, exceeds that of AmpB 2000-fold: Nagai, H.; Murata, M.; Torigoe, K.; Satake, M.; Yasumoto, T. J. Org. Chem. 1992, 57, 5448-5453. As occurs with AmpB, the higher sensitivity of fungal cells to gambieric acids action, probably originates from its higher affinity for ergosterol-containing membranes (fungal cells) as compared to cholesterol-containing membranes (mammalian cells): Bolar, J.; Legrand, P.; Heitz, F.; Cybulska, B. Biochemistry 1991, 30, 5707-5715.
22. Manta, E.; Scarone, L.; Hernández, G.; Mariezcurrena, R.; Suescun, L.; Brito, I.; Brouard, I.; González, M.C.; Pérez, R.; Martin, J.D. Tetrahedron Letters 1997, 38, 5853-5856 and references quoted therein.
23. Köning, B.; Horn, C. Syn Lett 1996, 1013-1014.
24. Álvarez, E.; Delgado, M.; Díaz, M.T.; Hanxing, L.; Pérez, R.; Martín, J.D. Tetrahedron Letters 1996, 37, 2865-2868.
25. (a) Schwab, P.; France, M.B.; Ziller, J.W.; Grubbs, R.H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039-2041.
26. (b) Zuereher, W.J.; Hashimoto, M. Grubbs, R.H. J. Am. Chem. Soc. 1996, 118, 6634-6640, and references cited therein.
27. 13CNMR, MS, and IR and gave satisfactory elemental analyses.