Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives,The Journal of Organic Chemistry

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Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyn-Tethered Indoles To Prepare Rutaecarpine Derivatives
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2018-02-02 00:00:00 , DOI: 10.1021/acs.joc.7b02956
Xiang-Fei Kong _{1,

2} , Feng Zhan ₁ , Guo-Xue He ₁ , Cheng-Xue Pan ₁ , Chen-Xi Gu ₁ , Ke Lu ₁ , Dong-Liang Mo ₁ , Gui-Fa Su ₁

Affiliation

An efficient method to synthesize rutaecarpine derivatives via the gold-catalyzed selective cyclization of alkyn-tethered indoles under mild conditions is described. The alkyn-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation. Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp³ and sp² hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride.

中文翻译：

黄金催化的炔烃连接的吲哚的选择性6 -exo-dig和7 -endo-dig环化反应，以制备芸苔芸香碱衍生物

描述了一种在温和条件下通过金催化的炔键连接的吲哚的选择性环化反应合成芸香果碱衍生物的有效方法。炔键连接的吲哚可以通过氧化和顺序金催化进行6 -exo-dig环化反应，而通过金催化和顺序氧化进行7 -endo-dig环化反应。底物范围研究表明，环化的选择性受底物与喹唑啉酮中2位碳的sp ³和sp ²杂交的控制。此外，从伊豆酸酐中分四步容易地以克级制备了芸香果碱支架，产率为67％。

更新日期：2018-02-02

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