Synthesis and Characterization of Novel Aryl Cyclitols: Polycyclitols

Abstract

New polycyclitols were synthesized starting from 1,4-naphthoquinone. An endo-selective Diels-Alder cycloaddition between 1,4-naphthoquinone and 1-acetoxybutadiene afforded a diketone. Reduction of the diketone with a NaBH4-CeCl(3)7H(2)O system gave a new cyclitol analog diol acetate. Acetylation of this compound afforded a triacetate. Oxidation of the double bond of the triacetate compound with OsO4 followed by acetylation of hydroxyl groups gave the pentaacetate, whose structure was established unequivocally via application of x-ray crystallographic methods. Hydrolysis of ester groups of pentaacetate under basic condutions furnished the desired and another novel aryl cyclitol.