Synthesis of 4′-C, 3′-O bicyclic thymidine analogues using ring closure metathesis

We have developed a route to the synthesis of new six-membered ring bicyclic nucleoside analogues. The synthesis of 4′-C, 3′-O bicyclic thymidine analogues is presented as first examples of this new family. Six-membered ring construction was efficiently achieved by the application of ring closure olefin metathesis on a diene intermediate using Grubbs’ catalyst.