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-CeCl3 · 7H2O 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.
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GRAPHICAL ABSTRACT
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