Total Synthesis and Reconfirmation of the Absolute Configuration of Melanochromone

Herein, we present the first regioselective total synthesis of the natural chromone (3’R)-melanochromone (2), along with its enantiomer (3’S)-melanochromone (1), and the structurally related chromones greveichromenol (3) and ledebouriellol (4). The synthesis was accomplished using the readily available trihydroxyacetophenone as the starting material and the well-established Jacobson’s asymmetric epoxidation method. Although chromones 1-4 did not demonstrate significant anti-inflammatory activity, our synthetic approach provides a viable strategy for further exploration of this class of natural chromones.