Synthesis of neo and gala-quercitol with a new method

A method for preparing two new quercitol having a gala- and neo- quercitol construction is described. 1,2-dibromo cyclohexadiene that is formed from brominaton of 1,4-cyclohexadiene, was reacted with mCPBA for revised epoxydation. Cleavage of epoxy in acidic condition and ketalization (2,2-dimethoxy propane/DMF/pTSA) of formed diols, gave trans-5,6-dibromo-dimethylhexahydro-1,3-benzo-trans-dioxol. The reaction of trans-5,6-dibromo-dimethylhexahydro-1,3-benzo-trans-dioxol with NaOMe gave (3aS,5R,7aS)-5-methoxy-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[d][1,3]dioxol.The synthesis of o-methyl gala- and neo- quercitol was realyzed that the hydrolization and acetylation of oxidized product, form the cis- and trans- hydroxylation of benzenedioxol. Hydrolization of the quercitols with HBr 32% gave gala- and neo- quercitol pentaacetate. Hydrolysing of the pentaacetates with NH3(g)/MeOH gave gala- and neo- quercitol.