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

本课题分两个小组进行，第一小组研究了碱催化的非对映选择性Diels-Alder（DA）反应，发现以（+）-亲双烯体和辛可尼定为光学活性胺催化剂，反应收率高达91%。亚组2首先研究了以易得的外消旋原料合成外消旋氨基环醇，并通过一个共同的中间体建立了有效胺和2-epivalidamine的高效合成路线;另一方面，研究了天然产物环己烯氧化物、（+）-epepoepoxy和（-）-phyllostine的不对称全合成，在本研究期间，使用可从我们的碱催化的3-羟基-2-吡喃酮的DA反应获得的手性构件也实现了。

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.