Synthesis of Oxaspirocyclohexadienones via Lewis‐Acid Catalyzed [2+3]‐Annulations of p‐Quinone Methides and Iodonium Ylides

Abstract

AbstractHerein, we report a mild method for the synthesis of oxaspirocyclohexadienones by using a combination of Lewis acid‐HFIP mediated [2+3]‐annulation of p‐quinone methides (p‐QMs) and iodonium ylides. The proposed mechanism proceeds through a one‐pot sequence of carbonyl activation/cyclopropyl formation/Cloke‐Wilson rearrangement to provide a broad range of oxaspirocyclohexadienones in moderate to high yields. Interestingly, the spiro‐annulated products were further converted to tetrahydroxanthane derivatives via BF3.OEt2 mediated dienone‐phenol rearrangement pathway. Moreover, the spiro‐annulated derivatives also showed a moderate anti‐tuberculosis activity against Mycobacterium tuberculosis H37Ra ATCC25177.