Author/Authors :
Choudhury، نويسنده , , Anusuya and Jin، نويسنده , , Fuqiang and Wang، نويسنده , , Dengjin and Wang، نويسنده , , Zhe and Xu، نويسنده , , Guoyou and Nguyen، نويسنده , , Dieu and Castoro، نويسنده , , John and Pierce، نويسنده , , Michael E. and Confalone، نويسنده , , Pat N، نويسنده ,
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.
Keywords :
nucleosides , purines , ?-hydroxylactone , ?-fluorolactone
