Researches on antiviral agents. 3. Synthesis and transformations of racemic and chiral 6-oxiranyl pyrimidinones

Article abstract of DOI:10.1016/S0040-4020(01)87190-8

The synthesis of epoxides 3, 4 and 6 has been described. The transformation of 3 into C-6 alkylated uracils 22a-e, 23a-d, 24 and 25 is also reported. The chiral epoxide (S)-(+)-3 has been prepared via a modified Solladie procedure, while the ZnCl_2- DIBAH reduction step failed to give the expected enantiomer (R)-(-)-3. This result has been discussed on the ground of molecular modeling studies.