Synthesis of substituted tetrahydrofuranones and tetrahydropyranones: Photocycloaddition/fragmentation reactions of dioxinones
1997; Elsevier BV; Volume: 38; Issue: 32 Linguagem: Inglês
10.1016/s0040-4039(97)01262-8
ISSN1873-3581
AutoresJay H. Dritz, Erick M. Carreira,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe 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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