Abstract
The highly functionalized THF 4 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 6 to THF 4 . The versatility of 4 was demonstrated by its conversion to bis-THF 3 , a known precursor for trilobacin, and to the tris-THF-lactone 5 , a potential relay compound for cyclic polyether analogues.
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