A novel method of preparing C-4' oxidized nucleotide, a monomeric model of
an alkali labile lesion (1) has been studied. The C-4' selenated 4a and 4b
were found to be effective in preparing 3, a monomeric model of 1, by the r
eaction with NBS (N-bromosuccinimide). The successive reaction of 3 with am
ine at room temperature afforded the alpha,beta-unsaturated gamma-methylene
-gamma-lactam (2) in good yield.