Synthesis of L- and D-4,6-Dideoxyhexoses and 4,6-Dideoxy-C-phenylglycosides from Enzyme-Generated Products

Optically active 1,3-diols 1 were prepared by biocatalysed routes. The synthetic versatility of compounds 1 as chiral building blocks was shown. The oxidative cleavage of the double bond afforded a carbonyl moiety, which allowed for elongation by Grignard addition and further derivatisation to make deoxy sugars readily available. The epoxidation of the same double bond allowed the direct intramolecular opening of the epoxide ring to generate deoxy C-phenylglycosides.