Synthesis of (±)-Brazilin Using IBX

A short synthesis of (±)-brazilin is reported. This synthesis uses several interesting and underutilized transformations including a regioselective dirhodium-catalyzed aryl C−H insertion, a regioselective IBX phenol → o-quinone oxidation, a tautomerization of an o-quinone to a p-quinone methide, and an intramolecular aryl cyclization with a p-quinone methide.