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首页> 外文期刊>Chemistry: A European journal >Trapped in Misbelief for Almost 40 Years: Selective Synthesis of the Four Stereoisomers of Mefloquine
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Trapped in Misbelief for Almost 40 Years: Selective Synthesis of the Four Stereoisomers of Mefloquine

机译：被误导困了近40年：甲氟喹的四种立体异构体的选择性合成

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摘要

Here we report the synthesis of all four stereoisomers of mefloquine. Mefloquine (Lariam) is an important anti-malaria drug that is applied as a racemate of the erythro form. However, the (-)-isomer induces psychosis, while the (+)-enantiomer does not have this undesired side effect. There are six syntheses of which five lead to the wrong enantiomer without the authors of these syntheses noting that they had synthesized the wrong compound. At the same time physical chemistry investigations had assigned the absolute configuration correctly and the last enantioselective synthesis that took these results into account delivered the correct absolute configuration. Since various synthetic approaches failed to provide the correct stereoisomers in previous syntheses, we submit here a synthetic approach with a domino Sonogashira-6π-electrocyclisation as key step that confirmed synthetically the correct absolute configuration of all four isomers.
机译：在这里，我们报告了甲氟喹的所有四个立体异构体的合成。 Mefloquine（Lariam）是一种重要的抗疟疾药物，被用作异型形式的外消旋体。然而，（-）-异构体引起精神病，而（+）-对映体没有这种不良副作用。有六种合成方法，其中五种导致错误的对映异构体，而这些合成方法的作者并未指出他们合成了错误的化合物。同时，物理化学研究正确地分配了绝对构型，并且考虑到这些结果的最后对映选择性合成提供了正确的绝对构型。由于各种合成方法都无法在以前的合成中提供正确的立体异构体，因此我们在此处提交了一种以多米诺Sonogashira-6π-电环化为关键步骤的合成方法，该合成方法可以确认所有四种异构体的正确绝对构型。

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