Stereoselective Synthesis of cis-2,5-Disubstituted Tetrahydrofuran-3-ones via an Acyl Radical Cyclization

Article abstract of DOI:10.1016/0040-4039(94)02162-5

Treatment of the acyl selenide 7 with triphenyltin hydride and triethylborane generates the acyl radical which undergoes 5-exo trigonal cyclization to afford the 2,5-disubstituted tetrahydrofuran-3-ones 10a/b in 97percent yield as a 94:6 mixture of diastereoisomers.