Cyclohexenyl nucleosides: Synthesis and biological activity of trans-3-(purin-9-yl)-4-cyclohexenylcarbinols

The primary alcohol of cis-3-hydroxy-4-cyclohexenylcarbinol was protected with a silyl group and then the configuration of the secondary alcohol was inverted (using Mitsunobu conditions, followed by deacylation). The secondary alcohol was converted to a carbonate, which, in turn, was converted to 6-chloropurine derivatives, using palladium coupling conditions. A modified deprotection procedure gave the free alcohol of these acid / base sensitive nucleoside analogs. The resulting 6-chloropurine derivatives were treated with ammonia, giving the 6-aminopurine derivatives which were finally converted with adenosine deaminase to the guanosine and inosine analogs. Copyright (C) 1996 Elsevier Science Ltd