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首页> 外文期刊>Chemistry: A European journal >Evolution of a Short Route to Strychnine by Using the Samarium-Diiodide-Induced Cascade Cyclization as a Key Step
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Evolution of a Short Route to Strychnine by Using the Samarium-Diiodide-Induced Cascade Cyclization as a Key Step

机译：Di二碘诱导的级联环化为关键步骤的士的宁短途路线的演变。

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摘要

This comprehensive report accounts the development of a highly diastereoselective samarium diiodide-induced cascade reaction of substituted indolyl ketones. The complexity-generating transformation with SmI2 allows the diastereoselective generation of three stereogenic centers including one quaternary center in one step. The obtained tetra- or pentacyclic dihydroindole derivatives are structural motifs of many monoterpene indole alkaloids, and their subsequent transformations gave way to one of the shortest approaches towards strychnine (14% overall yield in ten steps, or 10% overall yield in eight steps). During the course of this report we discuss the influence of substituents on the cyclization step, plausible mechanistic scenarios for the SmI2-induced cascade reaction, diastereoselective reductive amination, and regioselective dehydratization protocols towards the pentacyclic core structure of strychnos alkaloids.
机译：该综合报告说明了高度非对映选择性的二碘化mar诱导的取代吲哚基酮级联反应的发展。用SmI2生成复杂度的转换允许一步一步非对映地生成三个立体异构中心，包括一个四级中心。所获得的四环或五环二氢吲哚衍生物是许多单萜吲哚生物碱的结构基序，其随后的转化为最简单的方法（十步总收率为14％，八步总收率为10％）所取代。在本报告的过程中，我们讨论了取代基对环化步骤的影响，SmI2诱导的级联反应的合理机理，非对映选择性还原胺化和对选择性链霉菌生物碱的五环核心结构的区域选择性脱水方案。

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