Enantioselective synthesis of the alcohol moiety of dolabriferol.

Dolabriferol is a marine polypropionate characterized by an unusual noncontiguous carbon backbone. The two polypropionate subunits are linked by an ester function. The protected alcohol moiety of dolabriferol was synthesized via the enzymatic desymmetrization of meso-(anti-anti)-2,4-dimethyl-1,3,5-pentanetriol.

Stereoselective reduction of ketones by Daucus carota hairy root cultures.

Reduction of acetophenone by Daucus carota hairy root cultures afforded (S)-phenylethanol in high yield (96%) and excellent enantiomeric excess (ee>or=98%). Aromatic ketones, keto esters, and a simple aliphatic ketone were reduced with good stereoselectivity (ee=62-98%) and moderate to high chemical yields (25-90%).