导向氧化环化至吲哚的 C2-或 C4-位：welwitindolinones 双环[4.3.1]癸烷核心的高效构建。
Directed oxidative cyclizations to C2- or C4-positions of indole: efficient construction of the bicyclo[4.3.1]decane core of welwitindolinones.
机构信息
Department of Chemistry, The University of Chicago, 5735 South Ellis Avenue, Chicago, Illinois 60637, USA.
出版信息
Org Lett. 2011 Jun 17;13(12):3214-7. doi: 10.1021/ol201122f. Epub 2011 May 26.
Abstract
Regiocontrolled oxidative cyclizations of 3-substituted indoles are described herein. Specifically, it is shown that the installation of a chloride at C2 alters the inherent propensity for cyclization at the 2-position of indole so as to favor the 4-position, enabling the construction of the unique framework found in most welwitindolinone alkaloids. The chloride functions here as more than a blocking group, as it also provides ready access to the corresponding oxindole.
摘要
本文描述了 3-取代吲哚的区域控制氧化环化反应。具体而言，研究表明在 C2 位引入氯原子会改变吲哚 2-位环化的固有倾向，有利于 4-位，从而构建大多数威尔维丁螺酮生物碱中存在的独特骨架。氯原子在这里不仅起到了阻断基团的作用，还提供了通往相应的氧化吲哚的便捷途径。
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