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Note | Regular issue | Vol 53, No. 1, 2000, pp.219-224
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8740
An Efficient Synthesis of (±)-cis-2-Amino-6-hydroxy-9-[4’-hydroxyethyl-2’-cyclopenten-1’-yl]purine

Won Kim, Hyangdug Kim, and Hakjune Rhee*

*Department of Chemistry, Hanyang University, Ansan, Kyunggi-do 425-791, Korea

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.