Synthetic study of optically active aminocyclitols ; possible drugs for diabetes.

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This project was carried out by two subgroups.Subgroup 1 examined a diastereoselective base-catalyzed Diels-Alder (DA) reaction With several optically active dienophiles, and found that the reaction gave desired product up to 91 %de by using (+)-dienophile and cinchonidine as an optically active amine catalyst. This reaction was suitable for the starting material of the asymmetric synthesis of titled compounds.Subgroup 2 first studied the synthesis of racemic aminocyclitols using readily obtained racemic starting material, and established the afficient synthetic route toward validamine and 2-epivalidamine via a common intermediate.On the other hand, an asymmetric total synthesis of naturally occurring cyclohexeneoxides, (+)-epiepoformin and (-)-phyllostine, has been also achieved using the chiral building block available from our base-catalyzed DA reaction of 3-hydroxy-2-pyrone in this study period.