Total Synthesis of Vestitol and Medicarpin

Abstract Total synthesis of vestitol and medicarpin, two isoflavonoids with distinct skeletons, was successfully achieved using a single intermediate as the starting point. This six-step synthetic approach features a BBr3-promoted tandem O-demethylation/cyclization reaction, which enables the rapid construction of the pterocarpan core structure. Subsequently, a Pd/C-catalyzed hydrogenation/hydrogenolysis reaction was employed to respectively synthesize vestitol and medicarpin.