Convenient Synthesis of Disubstituted Cyclic Ethers. Syntheses of (-)-cis-Rose Oxide and (cis-6-Methyltetrahydropyran-2-yl)acetic Acid

Article abstract of DOI:10.1246/cl.1999.893

Disubstituted cyclic ethers are stereoselectively prepared on the successive treatment of δ- or ε-lactones with t-butyldimethylsiloxy-1-ethoxyethene and silyl nucleophiles in the presence of a catalytic amount of trityl hexachloroantimonate or a catalyst system of antimony pentachloride, chlorotrimethylsilane and tin(II) iodide.The present procedure is effectively applied to short syntheses of (-)-cis-rose oxide and (cis-6-methyltetrahydropyran-2-yl)acetic acid, a constituent of civet.