Stereospecific synthesis of chiral caprolactone monomers from d-glucose

The synthesis and characterisation of a novel chiral bicyclic oxacaprolactone is reported. The choice of diisopropylidene-d-glucose as a starting material allowed selective introduction of the synthetic equivalent necessary for the formation of the seven-membered ring of the lactone, i.e., one carbon atom and the carbonyl of the ester which was to become the carbonyl group of the lactone. In order to complete the formation of the seven-membered ring, via intramolecular lactonisation, it was necessary to excise carbon six and to establish a primary alcohol group at C-5. The lactone was fully characterised and available for ring-opening polymerisation.