Enzymatic Approach to Enantiomerically Pure 5-Alken-2,4-diols and 4-Hydroxy-5-alken-2-ones: Application to the Synthesis of Chiral Synthons

Enantiomerically pure 1,3-diols 1−3 were obtained by a chemoenzymatic approach (lipase PS from
Burkholderia cepacia). These diols were converted into useful chiral synthons, which could be considered
homologues of glyceraldehyde and glyceric acid acetonides. Applications of these synthons to the de
novo synthesis of sugars and preparation of conagenin carboxylic moiety were shown. Hydroxy ketone
4 was chosen as a model system for another synthetic evolution:  it was obtained in enantiomerically
pure form by enzymatic resolution and converted into chiral tetrahydropyranes, such as the stereoisomers
of the commercial fragrance Gyrane.