Synthetic approaches to (±)-c-4-amino-r-1,c-2,t-3-cyclopentanetrimethanol: a precursor of higher homologues of xylo-carbocyclic nucleosides

Aminoalcohol , a compound of interest for the synthesis of carbocyclic analogs of nucleosides, was prepared from (±)-(2endo,3exo)bicyclo[2.2.1]hept-5-ene-2,3-dimethanol. In the key step, oxidative degradation of a carboxamide was efficiently achieved by treatment of amidoester with lead tetraacetate in tert-butanol.