The reaction of 2-(trimethylsiloxy)furans with lead(IV) acetate afforded the corresponding α,β-unsaturated γ-acetoxy-γ-lactones in good yields. The lactones were easily converted into the corresponding 3-acylacrylic acids. Utilizing this reaction, dl-pyrenophorin was synthesized.
Chemistry of 2,5-bis(trimethylsiloxy)furans. III: Synthesis of γ-hydroxybutenolides
作者:Peter Brownbridge、Tak-Hang Chan
DOI:10.1016/s0040-4039(00)78707-7
日期:1980.1
γ-Hydrobutenolides were obtained from the reaction of substituted 2,5- bis(trimethylsiloxy)furans with aldehydes and ketones using titanium tetrachloride activation. Similarly, α,β-unsaturated carbonyl compounds reacted as a Michael receptor with the title compounds to give γ-hydroxybutenolides.