Enantioselective enzymatic synthesis of the anti-viral agent lamivudine (3TC)

Article abstract of DOI:10.1016/0040-4039(95)01380-Z

A novel enzymatic resolution of α-acetoxysulfides has been used as the key step in the synthesis of the important antiviral nucleoside analogue lamivudine. The synthesis proceeds via a configurationally stable hemithioacetal which cyclises in situ to form the required oxathiolane nucleus, which can then be converted into the target nucleoside in 4 steps.