A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone |
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Authors: | Anusuya Choudhury Fuqiang JinDengjin Wang Zhe WangGuoyou Xu Dieu NguyenJohn Castoro Michael E PiercePat N Confalone |
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Institution: | Bristol-Myers Squibb Pharma Company, Research & Development, Chambers Works, Deepwater, NJ 08023-0999, USA |
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Abstract: | Anti-HIV agent β-F-ddA (1) has been synthesized starting from readily available non-sugar, (S)-(+)-Dihydro-5-(hydroxymethyl)-2-(3H)-furanone (4). A highly syn-stereoselective fluorination of the hydroxy lactone 2 generates the key intermediate fluorolactone 5 in a short and concise synthetic sequence. Reduction of 5 followed by bromination generates the aglycon which is glycosylated to generate F-ddA by amination and deprotection. Steric bulk of the 5-protecting group has minimal effect on the steric course of glycosylation. |
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Keywords: | nucleosides purines β-fluorolactone α-hydroxylactone |
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