Chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane, precursor for carbocyclic nucleoside synthesis. Dieckmann cyclization with an alpha-amino acid

A new method for the synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane, a precursor in the synthesis of some carbocyclic nucleoides, is discussed. The method includes three steps: the synthesis of (S)-2-aminoadipic acid; Dieckmann cyclization to an aminocyclopentanone; and derivatization of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane. The importance of carbocyclic nucleotides lie in their antiviral and antineoplastic properties.