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http://dx.doi.org/10.5012/bkcs.2008.29.10.1977

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

Kim, Kyung-Ran (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Park, Ah-Young (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Lee, Hyung-Rock (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Kang, Jin-Ah (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Kim, Won-Hee (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Chun, Pu-Soon (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Bae, Jang-Ho (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Jeong, Lak-Shin (Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University)
Moon, Hyung-Ryong (Laboratory of Medicinal Chemistry, College of Pharmacy and Research Institute for Drug Development, Pusan National University)
Publication Information
Abstract
Novel bicyclo[3.1.0]hexanyl purine nucleoside analogues were synthesized as potential antiherpetic agents via a bicyclo[3.1.0]hexanol (${\pm}$)-8, which was prepared using a highly efficient carbenoid cycloaddition reaction. A highly diastereoselective reduction of ketone and a Mitsunobu reaction for the condensation of glycosyl donor (${\pm}$)-12 with 6-chloropurine were employed.
Keywords
Bicyclo[3.1.0]hexanone; Intramolecular carbenoid cycloaddition; Mitsunobu reaction; Diastereoselective reduction; North conformation
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