Short and scalable synthesis of cynandione A.

A two-step gram-scale synthesis of cynandione A is described. The key to success is the one-pot tandem oxidation/regioselective arylation of 1,4-hydroquinone in the presence of an excess amount of oxidant. Natural bond orbital charge analysis was performed in order to understand the regioselectivity of the arylation step. The highly practical and scalable synthesis developed herein is expected to assist the in-depth biological evaluation of cynandione A in various animal models.