Lewis Acid Catalyzed Tandem 1,4-Conjugate Addition/Cyclization of in Situ Generated Alkynyl o-Quinone Methides and Electron-Rich Phenols: Synthesis of Dioxabicyclo[3.3.1]nonane Skeletons

被引：41

作者：

Du, Ji-Yuan ^{[1
]}

Ma, Yan-Hua ^{[1
]}

Meng, Fan-Xiao ^{[1
]}

Chen, Bao-Li ^{[1
]}

Zhang, Shao-Liang ^{[1
]}

Li, Qjan-Li ^{[1
]}

Gong, Shu-Wen ^{[1
]}

Wang, Da-Qi ^{[1
]}

Ma, Chun-Lin ^{[1
]}

机构：

[1] Liaocheng Univ, Coll Chem & Chem Engn, Liaocheng 252059, Shandong, Peoples R China

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 14期

关键词：

ENANTIOSELECTIVE 4+2 ANNULATION; ARTOCARPUS-HETEROPHYLLUS; ASYMMETRIC-SYNTHESIS; ALLENIC ESTERS; VINYL-CATION; FLAVONOIDS; CYANOMACLURIN; DIHYDROCOUMARINS; SALICYLALDEHYDES; CYCLOADDITION;

D O I：

10.1021/acs.orglett.8b01862

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A versatile Lewis acid catalyzed tandem cyclization of in situ generated alkynyl o-quinone methides (o-AQMs) with electron-rich phenols has been developed on the basis of the mode involving an intermolecular 1,4-conjugate addition/6-endo cyclization/1,3-aryl shift/intra-molecular 1,4-conjugate addition cascade. This reaction provides a new method for expeditious assembly of synthetically and biologically interesting tetracyclic bridged dioxabicyclo[3.3.1]nonane skeletons featuring a congested bridgehead oxa-quaternary stereocenter.

引用

页码：4371 / 4374

页数：4

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