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

Abstract

Aminoalcohol 3 , a compound of interest for the synthesis of carbocyclic analogs of nucleosides, was prepared from (±)-(2 endo,3 exo)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 10 with lead tetraacetate in tert-butanol.