1,2-O-Isopropylidene-5-alkene templates for the synthesis of oligo-tetrahydrofurans

The highly functionalized THF was prepared in eight steps from 2,5-cyclooctadiene. The key step in this synthesis was a novel desymmetrization reaction involving the iodoetherification of the C2 symmetric bis-isopropylidene alkene to THF . The versatility of was demonstrated by its conversion to bis-THF , a known precursor for trilobacin, and to the tris-THF-lactone , a potential relay compound for cyclic polyether analogues.