An expeditious and efficient procedure for the synthesis of unsaturated acyclonucleosides of Z configuration related to D4T

Enantiopure 2,5-dihydrofuran derivatives were prepared from (S)-glycidol through a new reaction sequence involving epoxide opening with a vinyleuprate, selenium-induced cyclization to give exclusively the 5-endo product, and regioselective selenoxide elimination. Unsaturated acy-clonucleosides of Z configuration were obtained in a straightforward manner by treating 2,5-dihydrofuran with iodotrimethylsilane in the presence of silylated purinic or pyrimidinic bases. This synthetic process involves opening of the dihydrofuran ring by trimethylsilyl iodide and substitution of iodine by the nucleic base in a single reaction step.