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Enantioselective total synthesis of the potent anti-HIV nucleoside EFdA
Masayuki Kageyama1, Tomohiro Nagasawa, Mayumi Yoshida
1Laboratory of Applied Bioorganic Chemistry, Graduate School of Agricultural Science, Tohoku University, Tsutsumidori-Amamiyamachi, Sendai 981-8555, Japan.
Abstract:
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.
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