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Enantioselective Total Synthesis of the Potent Anti-HIV Nucleoside EFdA

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journal contribution
posted on 07.10.2011, 00:00 by Masayuki Kageyama, Tomohiro Nagasawa, Mayumi Yoshida, Hiroshi Ohrui, Shigefumi Kuwahara
A concise enantioselective total synthesis of 4′-ethynyl-2-fluoro-2′-deoxyadenosine (EFdA), an extremely potent anti-HIV agent, has been accomplished from (R)-glyceraldehyde acetonide in 18% overall yield by a 12-step sequence involving a highly diastereoselective ethynylation of an α-alkoxy ketone intermediate.