S. Bergmeier, A. Cobas, H. Rapoport
Apr 1, 1993
Citations
0
Influential Citations
48
Citations
Journal
Journal of Organic Chemistry
Abstract
Carbocyclic nucleosides are important isosteres of nucleosides possessing a variety of antiviral and antineoplastic activities. We report here a new method for the chirospecific synthesis of (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane. This compound is a key precursor for the synthesis of some carbocyclic nucleosides. The method involves (1) an improved synthesis of (S)-2-aminoadipic acid; (2) Dieckmann cyclization of this α-amino acid to an aminocyclopentanone; and (3) elaboration of the latter to the target (1S,3R)-1-amino-3-(hydroxymethyl)cyclopentane. The starting (S)-2-aminoadipic acid 6-methyl ester was prepared enantiomerically pure from (S)-aspartic acid in 51% overall yield