Total Synthesis of Norbadione A

A short, convergent synthesis of the mushroom pigment norbadione A is described. The construction of an appropriately substituted naphtholactone intermediate involved a regioselective Diels−Alder reaction between a bis(triisopropylsilyloxy)diene and 2,6-dichlorobenzo-1,4-quinone. A double Suzuki−Miyaura cross-coupling between a diboronate and two identical enol triflates was another key feature of the synthesis.