An Efficient Synthesis of (±)-cis-2-Amino-6-hydroxy-9-[4-hydroxyethyl-2-cyclopenten-1-yl]purine

Abstract

The synthesis of a carbovir analogue, (+/-)-cis-2-amino-6-hydroxy-9-[4'-hydroxyethyl-2'-cyclopenten-1'-yl]purine (2) was achieved from 2,5-norbornadiene (3) in six steps and 31% overall yield. This route involves a Meinwald rearrangement, one-pot operation (acid-hydrolysis and subsequent sodium borohydride reduction), and a Pd(0)-catalyzed coupling reaction.