Biomimetic total synthesis of Horsfiequinone B enabled by a Friedel–Crafts alkylation (FCA)-type non-homodimerization†

Abstract

The first and biomimetic total synthesis of horsfiequinone B was achieved in 13 steps. The synthesis featured two pivotal transformations, involving Brønsted acid (BA)-catalyzed Friedel–Crafts alkylation (FCA)-type non-homodimerization and [Cu(CH₃CN)₄]PF₆/DBED-catalyzed C(sp²)–H aerobic oxidation. Notably, the developed dimerization methodology is expected to enable diverse syntheses of other dimeric diarylpropane analogues, and to facilitate further investigations on structure–activity relationship and in-depth study of bioactivity.