Stereoselective Total Synthesis of Stereoisomers of Entecavir

Practical methods for the synthesis of three stereoisomers of Entecavir have been developed. Starting from the reported intermediate (1S,2R)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol and (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol, respectively, three stereoisomers of Entecavir have been prepared with 17-20% overall yields. In principle, other stereoisomers could also be prepared by using the materials and reactions described in this article.

Automated summary

Practical methods for the synthesis of three stereoisomers of Entecavir have been developed using the reported intermediates (1S,2R)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol and (1R,2S)-2-((benzyloxy)methyl)cyclopent-3-en-1-ol. The overall yields of the three stereoisomers are 17-20%. Other stereoisomers could also potentially be synthesized using the materials and reactions described in this article.