Synthetic Studies of Isoquinoline and Indole Alkaloids Using Asymmetric Catalysis

吲哚类和异喹啉类生物碱具有很强的生物活性。尽管在某些情况下，对映异构体具有不同的生物活性，但目前还没有一种通用的合成方法来选择性地合成这两种对映体。我们利用有机催化剂和有机铜试剂研究了生物碱的两个对映体的不对称合成的进展，发现了异喹啉和b-咔啉部分的几个不对称加成反应。这些反应产物被用于几种生物活性生物碱的不对称合成。该反应还用于合成具有α-葡萄糖苷酶抑制活性的海洋生物碱苏豆素A和硫代半硫酸盐A。

There have been various kinds of indole and isoquinoline alkaloids which have intense bioactivity. Although it has been known for several cases that enantiomeric isomers have different bioactivities, there are no general synthetic method that is useful for the selective synthesis of both enantiomers. We have been studying the development of asymmetric synthesis of both enantiomers of alkaloids by the use of organocatalysts and organocopper reagents, and found several asymmetric addition reactions to isoquinoline and b-carboline moieties. these reaction products were applied to the asymmetric synthesis of several bioactive alkaloids. The reaction was also used for the preparation of schulzeine A and penasulfate A, both of which are marine alkaloids having a-glucosidase inhibitory activity.