Stereoselective Synthesis of 3,4‐Dihydroxylated Prolines and Prolinols Starting from L‐Tartaric Acid
Stereoselective Synthesis of 3,4‐Dihydroxylated Prolines and Prolinols Starting from L‐Tartaric Acid
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DOI：
10.1002/jhet.1634
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发表时间：
2014
影响因子：
2.4
通讯作者：
M. Oba;Shinichi Koguchi;K. Nishiyama
中科院分区：
文献类型：
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作者：
M. Oba;Shinichi Koguchi;K. Nishiyama
介绍了3，4-二羟基脯氨酸和3，4-二羟基脯氨醇的直接立体选择性合成方法。该合成的关键反应是由L-酒石酸衍生的手性酰亚胺中间体的保护基团控制的非对映选择性氰化反应。3，4-二羟基谷氨酸甲酯经甲醇解得到3，4-二羟基谷氨酸甲酯，再通过内酰胺的羧基和酯基逐步还原为3，4-二羟基丙氨酸和3，4-二羟基丙氨醇。
A straightforward and stereoselective synthesis of 3,4-dihydroxyprolines and 3,4-dihydroxyprolinols is described. The key reaction in this synthesis is a protective group-controlled diastereoselective cyanation of a chiral acyliminium intermediate derived from l-tartaric acid. Methanolysis of the obtained cyanolactam gave methyl 3,4-dihydroxypyroglutamate that was converted to 3,4-dihydroxyproline and 3,4-dihydroxyprolinol by reduction of the lactam carbonyl and ester groups in a stepwise manner.