Enantiospecific and Stereoselective Synthesis of Polyhydroxylated Pyrrolidines and Indolizidines from <i>trans</i>-4-Hydroxy-<scp>l</scp>-proline
作者:María-Jesús Blanco、F. Javier Sardina
DOI:10.1021/jo9604245
日期:1996.1.1
We have developed a short, efficient, and stereoselective synthesis of polyhydroxylated pyrrolidine and indolizidine glycosidase inhibitors starting from 4-hydroxy-L-proline. The regio- and stereoselective hydroxylation of an N-Pf-4-oxoproline enolate and the stereoselective reduction of the resulting keto alcohol allowed us to introduce the cis diol present in the target compounds. The different side
我们从4-羟基-L-脯氨酸开始开发了一种多羟基化的吡咯烷和吲哚并立苷糖苷酶抑制剂的简短,有效和立体选择性的合成方法。N-Pf-4-氧代脯氨酸烯醇的区域和立体选择性羟基化以及所得酮醇的立体选择性还原使我们能够引入目标化合物中存在的顺式二醇。通过还原取代的脯氨酸的酯基或通过有机锂或有机镁试剂与相同基团的反应,然后立体选择性地还原所得的酮,来引入完成目标化合物合成所需的不同侧链。如此获得的醇经氢解得到所需吡咯烷糖苷酶抑制剂的盐酸盐,分九步获得,总收率超过50%。也使用该方法制备了吲哚唑烷糖苷酶抑制剂8-表-swainsonine。