Medium ring ethers

The assembly of medium-ring ethers using C-0 or C-C bond forming protocols can be a profitable enterprise 13 nevertheless, it was of interest to determine if medium-ring ethers could be derived... 

Fujiwara K (2006) Total Synthesis of Medium-Ring Ethers from Laurencia Red Algae. 5 ... 

Two step synthesis of medium-ring ethers through the intermediacy of thionium ions followed by sulfide reduction. 

Contemporary Organic Synthesis 1 457 (1994) (Recent Developments in the Synthesis of Medium-Ring Ethers)... 

Crimmins MT, Emmitte KA (1999) Total Synthesis of (+)-Laurencin An Asymmetric Alkylation-Ring-Closing Metathesis Approach to Medium Ring Ethers. Org Lett I 2029... 

The photoisomerization of cyclobutanones to transient car-benes has been used as part of an interesting synthesis of muscarine (Pirrung and DeAmicis). Intramolecular oxetan formation has been used as part of novel syntheses of medium-ring ethers (1) and the tricyclo-octane (2) (Carless et al. Gleiter and Kissler). Cossy et al. have employed the photoreductive cycliza-... 

As part of the synthetic studies towards (+)-brasilenyne, we carried out detailed conformational analyses of several of the 9-membered ring ethers that were synthesized along the way. In view of the limited number of studies that address the conformational preferences for highly substituted medium ring ethers, we wish to describe some interesting observations as an epilog to this chapter. 

Synthesis of prelaureatin, laurencin, and the medium-ring ether parts of ciguatoxins 07Y502. 

Preparation of novel lH-1,2,3-, 2H-1,2,3-, lH-1,2,4- and 4H-1,2,4-triazole derivatives A patent review (2008—2011) 13EOT319. Progress (since 2000) in the synthesis of oxepanes and medium ring ethers 12T6999. 

Recent progress in the synthesis of oxepanes and medium ring ethers. Tetrahedron, 68, 6999-7018. (d) Vilotijevic, L, Jamison, T. F. (2009). Epoxide-opening cascades in the synthesis of polycyclic polyether natural products. Angewaudte Cheruie lutematioual Edition, 48, 5250-5281. (e) Snyder, N. L., Haines, H. M., Peczuh, M. W. (2006). Recent developments in the synthesis of oxepines. Tetrahedron, 62, 9301-9320. (f) For medium-ring thiacycles Rosowsky, A. 1972. In Weissberger, A., Taylor, E. C. (Eds.) Heterocyclic Compounds. Wiley, New York. Vol. 26. 

A.S. Kleinke, D. Webb, T.F. Jamison, Recent progress in the synthesis of oxepanes and medium ring ethers. Tetrahedron 68 (2012) 6999-7018. 

Crimmins MT, Emmitte KA, Choy AL. Ring closing metathesis of the formation of medium ring ethers the total synthesis of (—)-isolaurallene. Tetrahedron 2002 58(10) 1817-1834. 

Oishi, T., Shoji, M., Maeda, K., Kumahara, N., and Hirama, M. (1996) Extensive ring-expansion strategy for the enantioselective synthesis of the medium ring ethers, oxepene, oxocane, and oxonene, of ciguatoxin. Synlett, 1165-1167. 

Carling, R.W., Clark, J.S., and Holmes, A.B. (1992) Synthesis of medium ring ethers. Part 2. Synthesis of the firlly saturated carbon skeleton of Laurenda non-terpenoid ether metabolites containing seven-, eight- and nine-membered rings. J. Chem. Soc., Perkin Trans. I, 83-94. 

Crimmins, M.T. and Emmitte, K.A. (1999b) Total synthesis of (-l-)-laurendn an asymmetric alkylation-ring-dosing metathesis approach to medium ring ethers. Org. Lett., 1, 2029-2032. 

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