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A novel intramolecular Prins cyclization of (E)-5-(2-(hydroxymethyl)phenyl)pent-4-en-1-ol with aldehydes has been achieved using 10mol% BF3·Et2O to produce 1-(tetrahydropyran-3-yl)-1,3-dihydroisobenzofuran derivatives in good to excellent yields with high selectivity. Similar type of coupling with salicylaldehydes provides the trans-fused hexahydropyrano[3,2-c]chromene derivatives in excellent yields.
An ϒ,δ-unsaturated alcohol tethered with a hydroxyl group, that is, (E)-2-styrylbutane-1,4-diol (1) undergoes a smooth bicyclization with various aldehydes in the presence of 10mol% InBr3 and at 0°C to afford a novel series of hexahydro-1H-furo[3,4-c]pyran derivatives in good yields with high diastereoselectivity.
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