A unified synthetic strategy based on [4 + 2] cycloaddition of readily accessible coupling fragments was conceptualized for the racemic total synthesis of recently isolated bioactive merrilliaquinone and other closely related quinones such as gramineusquinone B as well as neolignan, magnoshinin. The present article discloses our efforts in this direction which culminated in the total syntheses of gramineusquinone B, iso-merrilliaquinone, iso-magnoshinin and 2-epi-3,4-dihydro magnoshinin.