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首页> 外文期刊>Chemistry: A European journal >InCl _3-mediated addition of indole to isatogens: An expeditious synthesis of 13-deoxy-isatisine A
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InCl _3-mediated addition of indole to isatogens: An expeditious synthesis of 13-deoxy-isatisine A

机译：InCl _3介导的向吲哚的吲哚加成反应：13-脱氧-艾替斯汀A的快速合成

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摘要

A strategy directed towards the total synthesis of isatisine A that involves several late-stage metal-catalyzed transformations that address the key carbon-carbon and carbon-heteroatom bond formations has been developed. As a part of this strategy, methods for the addition of indoles to isatogens that lead selectively to either 2,2-disubstituted N-hydroxyindolin-3-one or 2,2-disubstituted indolin-3-one compounds have been developed by employing InCl _3 as a catalyst or as the reagent. The present methods provide the first examples of the additions of indoles to the isatogen nucleus. To demonstrate its viability, the synthesis of 13-deoxy-isatisine A has been completed in ten steps from a known and easily available lactone. [Metal]-mediated: Methods for the addition of indoles to isatogens have been developed to prepare 2,2-disubstituted indolin-3-ones. The total synthesis of 13-deoxy-isatisine has been executed (see scheme) by featuring several [metal]-mediated reactions at the final stages, such as Sonogashira coupling, [Pd]-mediated nitro-alkyne cycloisomerization, and [In]-mediated addition of indole to an isatogen.
机译：已经开发出一种针对全麻木素A合成的策略，该方法涉及若干后期金属催化的转化，以解决关键的碳-碳和碳-杂原子键的形成。作为该策略的一部分，已经开发出了通过使用InCl开发将吲哚添加到能选择性地导致2，2-二取代的N-羟基吲哚-3-酮或2，2-二取代的吲哚-3-酮化合物的致病原中的方法。 _3作为催化剂或试剂。本发明方法提供了将吲哚添加到致癌物核中的第一个实例。为了证明其可行性，已经从已知且容易获得的内酯以十个步骤完成了13-脱氧-艾迪酸A的合成。 [金属]介导：已经开发了将吲哚添加到致病原中的方法，以制备2,2-二取代的吲哚-3-酮。通过在最后阶段进行几种[金属]介导的反应，例如Sonogashira偶联，[Pd]介导的硝基-炔烃环异构化和[In]-介导的吲哚添加到致病原中。

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