Amorfrutin C, a C-5 prenyl amorfrutin, its allyl analog and an amorfrutin C-5 aldehyde have been synthesized using a biomimetic strategy from non-aromatic precursors. In this approach, a dioxinone derived β,δ-diketo ester underwent a decarboxylative Pd(0) catalyzed prenyl migration to give a β,δ-diketo dioxinone, which readily aromatized giving the amorfrutin core. The introduction of prenyl and allyl moieties at the C-5 position of the scaffold was accomplished using a Claisen rearrangement. Alternatively, iodination, lithium-iodine exchange and trapping with DMF gave the amorfrutin aldehyde and an amorfrutin alcohol when excess n-BuLi was used.