ChemInform Abstract: Prins Cyclization to Tetrahydrofuran Units of Polyether Antibiotics: Remarkable Siloxy Effect for Stereocontrolled Cyclization

A novel route to substituted tetrahydrofurans is described, which is based on the Lewis acid-promoted Prins cyclization with side chain formation of carbon-carbon bond. Bishomoallylic silyl ethers, rather than the (chloro)benzyl ethers and esters, provide selectivity tetrahydrofurans, indicating the siloxy effect for facilitating the cyclization.