Synthesis of (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one from D-glucose via palladium(0)-catalysed rearrangement of a vinylic epoxide intermediate

Abstract

The transformation of D-glucose into (R)-4-hydroxy-2-benzyloxymethylcyclopent-2-en-1-one (3), a potential chiral synthon for the antibiotic (–)-pentenomycin I (4), has been achieved via the intramolecualr aldolisation–dehydration of the 2-hydroxy-4-oxo-aldehyde (9) which was obtained by two different routs, one of them involving palladium(0)-catalysed rearrangement of a vinylic epoxid intermediate.