Synthesis of substituted tetrahydrofuranones and tetrahydropyranones: Photocycloaddition/fragmentation reactions of dioxinones

Article abstract of DOI:10.1016/S0040-4039(97)01262-8

The combination of dioxinone aldol addition methodology and [2+2]-photocycloaddition/fragmentation reactions can provide access to substituted tetrahydrofuran-3-ones and tetrahydropyran-4-ones, subunits abundantly found in biologically active natural products. Intramolecular photocyclization of vinyl and allyl ethers with dioxinones, followed by fragmentation in alkaline MeOH (K₂CO₃) leads to tetrahydrofuran-3-ones and tetrahydropyran-4-ones, providing a practical route to versatile building blocks for complex molecule synthesis.