Synthesis of (3-(Phosphonomethoxy)pyrrolidin-1-yl) Derivatives of Pyrimidines and Purines: Analogues of 2′,3′-Dideoxynucleotides.

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.