Synthesis of [3-(phosphonomethoxy)pyrrolidin-1-yl] derivatives of pyrimidines and purines: analogues of 2′,3′-dideoxynucleotides

Abstract

Pyrrolidin-1-yl derivatives of pyrimidines and purines, incorporating the phosphonomethoxy group as a phosphate mimic, were prepared as analogues of 2′,3′-dideoxynucleotides. The heterocyclic bases uracil, thymine, cytosine, adenine and hypoxanthine were constructed upon the primary amino group of the N-aminopyrrolidine 7, which was prepared by reaction of the dibromide 6 with hydrazine.