New stereoselective synthesis of thiamphenicol and florfenicol from enantiomerically pure cyanohydrin: a chemo-enzymatic approach

Thiamphenicol and florfenicol have been synthesized stereoselectively from enantiomerically pure 4-methylsulfanyl-mandelonitrile, which was obtained by hydrocyanation reaction of 4-methylsulfanyl-benzaldehyde catalyzed by (R)-hydroxynitrile lyase of Badamu (Prunus communis L. var. dulcis Borkh, almond from Xinjiang, China). It was found to be a highly effective bio-catalyst for this reaction after an extensive screening.

A new and efficient route to the asymmetric syntheses of thiamphenicol and florfenical has been developed resulting in high ee and de values in 26% and 18% overall yields, respectively.