翻转为吲哚啉区域选择性和吲哚内酰胺 V 的合成。
Overturning indolyne regioselectivities and synthesis of indolactam V.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
出版信息
J Am Chem Soc. 2011 Mar 23;133(11):3832-5. doi: 10.1021/ja200437g. Epub 2011 Feb 25.
Abstract
We report the design and synthesis of an indolyne that displays a reversal in regioselectivity, in both nucleophilic addition and cycloaddition reactions, compared to typical 4,5-indolynes. Our approach utilizes simple computations to predict regioselectivity in reactions of unsymmetrical arynes. With this methodology, novel benzenoid-substituted indoles can be accessed with significant regiocontrol. Furthermore, the technology provides an unconventional tactic for the synthesis of C4-substituted indole alkaloids, as demonstrated by a synthesis of indolactam V.
摘要
我们报告了一种吲哚啉的设计和合成，与典型的 4,5-吲哚啉相比，它在亲核加成和环加成反应中表现出了反转的区域选择性。我们的方法利用简单的计算来预测不对称芳炔反应的区域选择性。通过这种方法，可以以显著的区域控制方式获得新型苯并取代吲哚。此外，该技术为 C4 取代吲哚生物碱的合成提供了一种非传统的策略，如吲哚内酰胺 V 的合成所示。
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