Abstract:

In the last decade, lamivudine has been one of the most successful drugs for the treatment of HIV as well as chronic Hepatitis B. It inhibits both type 1 and 2 of the human HIV reverse transcriptase and also the reverse transcriptase of hepatitis B in vitro. Although there are many reported syntheses for the isomerically pure lamivudine, most of them introduce the chiral 1,3-oxathiolane motif by either crystallization of the correct isomer from a racemic mixture, or by enzymatic hydrolysis/acetylation of the other stereoisomers. The main drawback of those methods is the great loss in yield, as no more than 50% yield could be obtained while maintaining high stereoselectivity, due to the nature of the kinetic resolution.