Synthesis of Methyl-substituted Bicyclic Carbanucleoside Analogs as Potential Antiherpetic Agents

Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, KoreaReceived July 28, 2008Novel bicyclo[3.1.0]hexanyl purine nucleoside analogues were synthesized as potential antiherpetic agents viaa bicyclo[3.1.0]hexanol (±)- 8, which was prepared using a highly efficient carbenoid cycloaddition reaction. Ahighly diastereoselective reduction of ketone and a Mitsunobu reaction for the condensation of glycosyl donor(±)-12 with 6-chloropurine were employed. Key Words : Bicyclo[3.1.0]hexanone, Intramolecular carbenoid cycloaddition, Mitsunobu reaction, Diastereo-selective reduction, North conformationIntroductionSince the discovery of acyclovir