American Chemical Society
ol8b01862_si_001.pdf (7.08 MB)

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

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journal contribution
posted on 2018-07-05, 02:13 authored by Ji-Yuan Du, Yan-Hua Ma, Fan-Xiao Meng, Bao-Li Chen, Shao-Liang Zhang, Qian-Li Li, Shu-Wen Gong, Da-Qi Wang, Chun-Lin Ma
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/intramolecular 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.