5-Methoxyflavenes and 6-methoxyflavenes were found to undergo stereoselective acid-catalyzed rearrangement to generate a range ofnovel chromeno[2,3-b]chromene derivatives. When subjected to an in vitro antiplasmodial growth inhibition assay using Plasmodium falciparum (3D7 line) the chromene analogues were shown to display IC50 values ranging from 6.8 to 39.8 μM.