Synthesis of D- and L-apio nucleoside analogues with 2'-hydroxyl group as potential anti-HIV agents |
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Authors: | Jin Dong Zhe Kwon Sung Hee Moon Hyung Ryong Gunaga Prashantha Kim Hea Ok Kim Dae-Kee Chun Moon Woo Jeong Lak Shin |
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Institution: | College of Pharmacy, Seoul National University, Seoul 151-742, South Korea. |
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Abstract: | The present work describes the asymmetric synthesis of D- and L-apio-2',3'-dideoxynucleoside analogues, 4 and 5 with 2'-hydroxyl group via a common intermediate 9, starting from D-galactose. Stereoselective dihydroxylation and deoxygenation through radical inversion were successfully employed to synthesize the key intermediate 12 with D-apio structure, while stereoselecetive hydroboration-oxidation was used for the synthesis of another key intermediate 18 with L-apio structure. |
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