Total Synthesis of (-)-Aristeromycin

Abstract
The carbocyclic analogue of adenosine, (-)-aristeromycin (2; 9-[1′R,2′S,3′R,4′R)-2′, 3′-dihydroxy-4′-(hydroxymethyl)-1′-cyclopentyl]-9H-purin-6-amine) is synthesized from inexpensive natural tartaric acid (3) via key intermediate 8 [(4R, 5S)-4,5-isopropylidenedioxy-3-methoxy-2-cyclopentenone]. The synthetic strategy allows the preparation of different 6-substituted analogues 17 of (-)-aristeromycin.

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