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Concise Synthesis of Spirocyclic, Bridged γ-Butyrolactones via Stereospecific, Dyotropic Rearrangements of β-Lactones Involving 1,2-Acyl and δ-Lactone Migrations

2008; American Chemical Society; Volume: 130; Issue: 32 Linguagem: Inglês

10.1021/ja803579z

1943-2984

Vikram C. Purohit, A.S. Matla, Daniel Romo,

Organic Chemistry Synthesis Methods

Dyotropic processes involving unprecedented 1,2-acyl migrations provide access to novel spirocyclic, bridged keto-gamma-lactones from a series of fused, tricyclic-beta-lactones, available via biscyclization of ketoacids including a new asymmetric variant. In addition, a spirocyclic bis-gamma-lactone was generated via a dyotropic process involving a 1,2-beta-lactone/sigma-lactone interchange. Overall, this sequence provides a simple, two-step process for conversion of diketoacids to complex spiro[5.n]alkanes bearing a contiguous tertiary carbon center, a quaternary carbon center, and a tertiary alcohol in the form of a bridging gamma-lactone.