10.1016/j.tetlet.2006.04.097
The research focuses on the synthesis of substituted 3-furan-2(5H)-ones, which are structural motifs found in numerous bioactive natural products. The methodology involves a Diels–Alder sequence using anthracene and maleic anhydride to form a lactone, which upon deprotonation and electrophilic quenching, yields α-substituted lactones. Key reactants include anthracene, maleic anhydride, sodium borohydride, and various electrophiles such as methyl iodide, allyl iodide, butenyl bromide, benzyl bromide, tributyltin chloride, diethyl chlorophosphate, and chlorotrimethylsilane. The experiments utilize techniques like flash vacuum pyrolysis (FVP) to convert alkylated lactones into 3-substituted furan-2(5H)-ones. The study also explores the challenges and limitations of using cyclopentadiene in such reactions and proposes an alternative route to overcome these issues. Analytical techniques such as 13C NMR and IR spectroscopy were employed to confirm the structure and successful functionalization of the synthesized compounds.