Nucleosides, Nucleotides and Nucleic Acids, v. 21, issue. 1, page. 65-72
Abstract
A number of carbocyclic nucleosides can be synthesized from ( +cis-4-amino-2-cyclopentene-1 -methanol (3). Carbocyclic amino alcohol 3 is a key intermediate that makes possible the efficient synthesis of the carbocyclic nucleosides. In this study we wish to report an efficient synthesis of carbocyclic amino alcohol 3 from inexpensive and readily available starting material. The synthetic route employed cyclopentadiene (4) as a starting material and proceeded in 38% overall yield through 6 steps involving a hetero Diels-Alder reaction and an aza-Claisen rearrangement.