STUDIES ON STRUCTURALLY SIMPLE α,β-BUTENOLIDES. III. BEHAVIOUR OF (-)-(S)-δ-HETEROSUBSTITUTED γ-METHYL-α,β-BUTENOLIDES TOWARDS NUCLEOPHILES. PROTOANEMONIN AS INTERMEDIATE IN AN ELIMINATION-ADDITION MECHANISM.

Article abstract of DOI:10.1016/S0040-4020(01)88539-2

The reactivity of the title compounds with different nucleophiles has been checked and it was shown that products from reaction with sodium phenylthiolate result from an elimination-addition process in which protoanemonin is the key intermediate.The synthesis of (-)-(R)-β-angelica lactone is reported for the first time.