Highly efficient synthesis of 2′,3′-didehydro-2′,3′-dideoxy-β-nucleosides through a sulfur-mediated reductive 2′,3′-trans-elimination. From iodomethylcyclopropanes to thiirane analogs

A very simple methodology to achieve 2′,3′-didehydro-2′,3′-dideoxy nucleoside derivatives was performed by means of the treatment of 2′-deoxy-2′-iodo-β-nucleosides with NaHS. The same procedure leads to thiiranes from iodomethylcyclopropane derivatives.