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An Expeditious Synthesis Of Β,Γ-Unsaturated Δ-Lactones: Useful Pharmacological Synthetic Intermediates, Li Xiong

Masters Theses

Two-carbon ring expansions of vinyl β-lactones, were carried out by Lewis acids (BF₃-Et₂O or Et₂AlCl) via an ionization/cation rearrangement. β,γ-unsaturated δ-lactones were produced as efficient protocols for the synthesis of bioactive substances.

Vinyl β-lactones were prepared via ring closure of corresponding unsaturated β-hydroxy acids. Differently structured substrates were examined to study the influence of the substituents on the rearrangement. Other factors, such as temperature, solvent and catalyst were also studied in search of suitable reaction conditions.

This method is moderately successful in providing fused-ring δ-lactones, but higher yields (so far total yield of 24.8%) …