Synthesis of an Isostegane from Matairesinol

Abstract

In a recent communication,¹ we reported that the inclusion of boron trifluoride etherate in a thallium(III) trifluoroacetate (TTFA)-induced oxidative aryl-benzyl coupling reaction dramatically altered its outcome in that demethylation of a-phenyl methyl ether no longer accompanied the cyclization. A preliminary investigation also revealed that use of the combined reagents improved the yield of the dibenzocyclooctadiene obtained from a non-phenolic aryl-aryl coupling of a 1,4-diaryl substituted butane.²