Stereoselective Synthesis of d‑5-Homo-4-selenoribose as a Versatile Intermediate for 4′-Selenonucleosides

Stereoselective synthesis of d-5-homo-4-selenoribose, serving as a versatile intermediate for the synthesis of 4′-selenonucleosides <b>12a</b>–<b>c</b>, was accomplished using Sharpless asymmetric epoxidation, regioselective cleavage of the α,β-epoxide, and stereoselective reduction of the ketone as the key steps

Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents

Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5′-OH for phosphorylation, 4′-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5′-Homo-4′-selenonucleosides (<i>n</i> = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity