Synthesis of 5-alkenylated d4T analogues via the Pd-catalyzed cross-coupling reaction

The target compounds 5-[N-(6-amino-hexyl)-acrylamide]-2 ' ,3 ' -didehydro-2 ' ,3 ' -dideoxy-uridine (12) and 5-{N-[5-(methoxycarbonyl)-pentyl]acrylami de}-2 ' ,3 ' -didehydro-2',3 ' -dideoxy-uridine (15) were prepared by the p alladium acetate-triphenylphosphine-catalyzed reaction of the 5 ' -O-acetyl -5-iodo-d4T analogue (3). These compounds 12 and 15 can be used to prepare nucleotide probes carrying fluorescent labels and were nevertheless screene d for their anti-HIV activity. The biological data demonstrated that none o f them were active against HIV-1.