ChemInform Abstract: Parallel Solution-Phase Synthesis of Mechanism-Based Cysteine Protease...
Transcript of ChemInform Abstract: Parallel Solution-Phase Synthesis of Mechanism-Based Cysteine Protease...
2002 amino acids, peptides
amino acids, peptidesU 0400
13 - 194Parallel Solution-Phase Synthesis of Mechanism-Based CysteineProtease Inhibitors. — Free allylic amines (V) react with carboxylicacids preloaded onto hydroxynitrobenzophenone resin to afford amides whichare epoxidated with dimethyldioxirane. Opening of the epoxides is achieved bythiol addition using support-bound guanidine base in refluxing THF to give analcohol which is oxidated with Dess–Martin periodinane. The present sequenceto synthesize cysteine protease inhibitors combines the use of liquid–liquidextractions, volatile or solid-supported reagents and support-bound scavengersto avoid column chromatographic purifications of intermediates. — (LEE,ALICE; ELLMAN, JONATHAN A.; Org. Lett. 3 (2001) 23, 3707-3709; Dep.Chem., Univ. Calif., Berkeley, CA 94720, USA; EN)
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