Tetrahedron Letters p. 5579 - 5582 (1997)
Update date:2022-08-05
Topics: Starting Materials Fragmentation Photocycloaddition Rearrangement and Stabilization
Dritz, Jay H.
Carreira, Erick M.
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.
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