A convenient synthesis of racemic 2'-deoxy carbocyclic thymidines lacking the 5'-methylene group

Article abstract of DOI:10.1016/S0040-4039(98)01929-7

A convenient synthesis of racemic 2'-deoxy carbocyclic thymidines lacking the 5'-methylene group is reported. Thus, appropriately protected nucleic acid bases are coupled to 3-cyclopentenol, 1, via the Mitsunobu reaction. Epoxidation of the protected thymine substituted cyclopentene gives the corresponding syn and anti-epoxides in a 4:1 ratio. Ring opening of the syn-epoxide by a variety of nucleophiles leads to the racemic 2'-deoxy carbocyclic thymidines lacking the 5'-methylene group.