A concise and general entry into (R)-4-hydroxy-2-substituted cyclopent-2-enones from D-glucose: chiral intermediates for the synthesis of PGE2, (–)-pentenomycin I, and allethrin

Abstract

A general strategy for the transformation of D-glucose into different 2-substituted (R)-4- hydroxy-cyclopent-2-enones is described. This has been illustrated by the synthesis of (R)-2-[(1,3-dithian-2-yl)methyl]-4-hydroxycyclopent-2-enone, (R)-2-benzyloxymethyl-4-hydroxycyclopent-2-enone, and (R)-2-allyl-4-hydroxycyclopent-2-enone, which are potential chiral synthons for prostaglandin E₂, the antibiotic (–)-pentenomycin I, and the synthetic insecticide allethrin, respectively. The second chiral synthon was obtained by two different routes, one of them involving a novel palladium(0)-catalysed rearrangement of a vinyloxirane intermediate.