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Communication | Special issue | Vol 25, No. 1, 1987, pp.33-41
Published online, 1st January, 1970
DOI: 10.3987/S-1987-01-0033
The Chemistry of Cyclic Vinyl Ethers 4: Cyclization of Unsaturated Cyclic Vinyl Ether Epoxides

Robert K. Boeckman, Jr., Jayaram R. Tagat, and Brian H. Johnston

*Department of Chemistry, University of Rochester, Rochester, NY 14627, U.S.A.

Abstract

The synthesis of [3Z,5S,6R] 2-[5,6-epoxy-undec-3-en-1-y1]-5,6-dihydro-4H- pyran (2) and [3Z,5S,6R] 2-[5,6-epoxy-undec-3-en-1-yl]-3,4-dihydrofuran (3) is outlined. Cyclization reactions of 2 and 3 catalyzed by various Lewis acids which proceed to afford spirocyclic ketals rather than the desired carbocycles are described.