Synthesis of (1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2-propanediol (Trametol) and (1R,2S)-1-(3′,5′-Dichloro-4′-methoxyphenyl)-1,2-…

Abstract

  (1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2- propanediol (Trametol, 3), a metabolite of the fungus Trametes sp. IVP-F640 and Bjerkandera sp. BOS55, was synthesized by employing Sharpless asymmetric dihydroxylation as the key step. Similarly, the (1R,2S)-isomer of 1-(3′,5′-dichloro-4′-methoxyphenyl)-1,2-propanediol (4), another metabolite of Bjerkandera sp. BOS55, was synthesized by asymmetric dihydroxylation.