Development of new method for synthesis of substituted some polihydroxy cyclic compounds

In the presented study, (3aR,7aS)-1,3,3a,4,7,7a-hexahydroisobenzofuran was used as key compound for the synthesis of various carbasugar analogues. In the beginning, the alkene moiety of the key compound was submitted to photooxygenation and afforded two hydroperoxides. Without any purification of them, reduction of hydroperoxides with titanium tetraisopropoxide catalyzed in the presence of dimethyl sulfide gave two alcohol isomers. Then, they were acetylated with Ac2O in pyridine and epoxidation of the double bond in the related structures with m-CPBA followed by hydrolysis of the acetate groups with NH3 in CH3OH resulted in the formation of epoxy alcohol isomers. These isomers were subjected to an trans-dihydroxylation reaction with acid (H2SO4) in the presence of water and acetylation of the free hydroxyl groups produced benzofuran triacetates. Furan ring-opening reactions of the triacetate products with sulfamic acid catalyzed and the subsequent hydrolysis of the acetate groups with ammonia gave the targeted cyclohexane pentols carbasugar-based. Finally, all products obtained in this thesis were separated and purified by chromatographic and crystallographic methods. Also, the structures of them were determined by using 1H-NMR and 13C-NMR spectra.