An enantioselective synthesis of the core unit of the non-nucleoside reverse transcriptase inhibitor taurospongin A

Abstract

An enantioselective formal synthesis of taurospongin A has been achieved. The key steps involve chelation-controlled reductions of β-ketosulfoxide and β-hydroxy ketone intermediates and Sharpless asymmetric epoxidation to construct the tertiary alcohol stereoselectively.