Stereoselective bioreduction for the resolution of racemic mixtures of bicyclo[3.3.1]nonane-2,6-dione using vegetables

Screening of various vegetables as biocatalysts for the stereoselective bioreduction and resolution of racemic bicyclo[3.3.1]nonane-2,6-dione was performed. Vegetables of the family Apiaceae, i.e. the roots of parsnip (Pastinaca sativa), celery (Apium graveolens), parsley (Petroselinum crispum) and carrot (Daucus carota) were found to be the best. The methodology described here allows the efficient enantioseparation of (+)-enantiomer of bicyclo[3.3.1]nonane-2,6-dione. The reaction time, temperature and the amount of celery roots were optimized and (+)-enantiomer was obtained with the optical purity of 90–98% and the yield of more than 90%.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► For the enantioseparation of racemic bicyclo[3.3.1]nonane-2,6-dione, vegetables of the family Apiaceae were found to be suitable. ► Reaction conditions were optimized using celery roots. ► (+)-Enantiomer of bicyclo[3.3.1]nonane-2,6-dione was obtained with the optical purity of 90–98% and the yield of more than 90%.