Rapid Access to a Cyclobutane-Containing Skeleton Fused with Chromane through In(III)-Catalyzed Intramolecular
Tao Jiang1, FuJunyang Wu1, Rong Xie1
1Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500, P.R. China.
Abstract:
Intramolecular oxidative annulation of 5-hydroxy benzochromene via In(OTf)3 and DDQ catalysis, through an ortho-quinone methide radical intermediate, afforded various cyclobutane-containing products in good to excellent yields. This oxidative annulation pathway reveals great group tolerance and broad compatibility with benzochromene. In addition, this method exhibits an excellent ability to synthesize cyclobutane-containing products in gram-scale experiments, providing a novel approach to synthesize a series of natural products, such as cannabicyclol, isoeriobrucinol A, and ranhuadujuanine A.
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