The total synthesis of (±)-mevashuntin, a structurally unique naturally occurring pyrano- naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels–Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the ...