Highly stereoselective preparation of (3R,4S)-3,4-chromanediol by deracemization of (±)-3-hydroxy-4-chromanone by Trichosporon cutaneum

Deracemization of (±)-3-hydroxy-4-chromanone 2 through stereoselective bioreduction to the corresponding (3R,4S)-3,4-chromanediol 3, with good to excellent enantiomeric excesses (up to 99%), mediated by resting cells of the yeast Trichosporon cutaneum CCT 1903, is reported. In addition, 3-hydroxychromone (7) was obtained as a secondary product.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide

(3R,4S)-3,4-ChromanediolC9H10O3Ee = up to 99%[α]D20=+77.5 (c 0.87, THF)Source of chirality: biocatalytic reductionAbsolute configuration: (3R,4S)