A concise synthesis of anti-viral agent F-ddA, starting from (S)-dihydro-5-(hydroxymethyl)-2(3H)-furanone

✍ Scribed by Anusuya Choudhury; Fuqiang Jin; Dengjin Wang; Zhe Wang; Guoyou Xu; Dieu Nguyen; John Castoro; Michael E Pierce; Pat N Confalone

• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 123 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(02)02532-7

✦ Synopsis

Anti-HIV agent b-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.