The first synthesis of the chromanone lactone dimer gonytolide A has been achieved employing vanadium (V) -mediated oxidative coupling of the monomer gonytolide C. An o-bromine blocking group strategy was employed to favor para para coupling and to enable kinetic resolution of (+/-)-gonytolide C. Asymmetric conjugate reduction enabled practical kinetic resolution of a chiral, racemic precursor and the asymmetric synthesis of (+)-gonytolide A and its atropisomer.