ChemInform Abstract: Parallel Solution-Phase Synthesis of Mechanism-Based Cysteine Protease...

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2002 amino acids, peptides amino acids, peptides U 0400 13 - 194 Parallel Solution-Phase Synthesis of Mechanism-Based Cysteine Protease Inhibitors. Free allylic amines (V) react with carboxylic acids preloaded onto hydroxynitrobenzophenone resin to afford amides which are epoxidated with dimethyldioxirane. Opening of the epoxides is achieved by thiol addition using support-bound guanidine base in refluxing THF to give an alcohol which is oxidated with Dess–Martin periodinane. The present sequence to synthesize cysteine protease inhibitors combines the use of liquid–liquid extractions, volatile or solid-supported reagents and support-bound scavengers to 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) 1

Transcript of ChemInform Abstract: Parallel Solution-Phase Synthesis of Mechanism-Based Cysteine Protease...

Page 1: ChemInform Abstract: Parallel Solution-Phase Synthesis of Mechanism-Based Cysteine Protease Inhibitors.

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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