94530-18-4Relevant academic research and scientific papers
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
Achab, Said,Das, Bhupesh C.
, p. 2863 - 2873 (2007/10/02)
A general strategy for the transformation of D-glucose into different (R)-4-hydroxycyclopent-2-enones is described.This has been illustrated by the synthesis of (R)-2--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.
