Multi-gram synthesis of a nucleotide-competing reverse transcriptase inhibitor
2013
Abstract An efficient multi-gram synthesis of a nucleotide-competing reverse transcriptase inhibitor is reported. The synthesis features a chiral auxiliary-assisted alcohol resolution, a Mitsunobu reaction involving a carbamate, followed by a lithium-iodide exchange/Weinreb ketone synthesis tandem. These chemical transformations were optimized in order to increase the yield of the synthesis. The route is concluded by a late-stage palladium-catalyzed cyanation followed by a pyrimidine-2-one ring formation.
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