A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes

Jia Guo; Xiaoshi Peng; Xiaoyu Wang; Fukai Xie; Xinhang Zhang; Guoduan Liang; Zenghui Sun; Yongxiang Liu; Maosheng Cheng; Yang Liu

doi:10.1039/C8OB02582G

A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes†

Jia Guo,‡^ab Xiaoshi Peng,‡^ab Xiaoyu Wang,^ab Fukai Xie,^abc Xinhang Zhang,^abc Guoduan Liang,^abc Zenghui Sun,^abc Yongxiang Liu,

^abc Maosheng Cheng^ab and Yang Liu

*^a

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* Corresponding authors

^a Key Laboratory of Structure-Based Drug Design and Discovery (Shenyang Pharmaceutical University), Ministry of Education, Shenyang 110016, P. R. China
E-mail: yongxiang.liu@syphu.edu.cn, mscheng@syphu.edu.cn

^b Institute of Drug Research in Medicine Capital of China, Benxi, P. R. China

^c Wuya College of Innovation, Shenyang Pharmaceutical University, Shenyang 110016, P. R. China

Abstract

A unique gold(I)-catalyzed 5-endo-dig cyclization/aerobic oxidation cascade strategy from 1,5-enyne substrates with molecular oxygen as the oxidant to yield the indenone was described. The reaction mechanism was studied by heavy atom labelling and some related experiments. This method was applied to the formal total synthesis of isoprekinamycin.

This article is part of the themed collection: Synthetic methodology in OBC

Organic & Biomolecular Chemistry

A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes†

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A gold-catalyzed cycloisomerization/aerobic oxidation cascade strategy for 2-aryl indenones from 1,5-enynes

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