Acidic hydrolysis and acetylation of epoxidation products 11a/b of 1,4-diacetoxy-2-cycloheptene afforded unsymmetrical 1,2,3,4-tetraacetoxycycloheptane (12). OsO4-cis-hydroxylation and acetylation of 1,4-diacetoxy-2-cycloheptene gave two symmetrical 1,2,3,4-tetraacetoxycycloheptanes (14/15). Deacetylation of 1,2,3,4-tetraacetoxy cycloheptanes gave cycloheptane-1,2,3,4-tetraols as cyclitol mimetics.
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