Parallel solution-phase synthesis of mechanism-based cysteine protease inhibitors.
[reaction--see text] A seven-step parallel solution-phase synthesis has been developed for access to ketone-containing mechanism-based cysteine protease inhibitors. The use of liquid-liquid extractions, volatile or solid-supported reagents, and resin-bound scavengers eliminates the need for intermediate column chromatographic purification during this synthesis sequence.
Lee
A
A
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, USA.
Ellman
J A
JA
D000577:Amides / Q000737:chemistry; D015853:Cysteine Proteinase Inhibitors / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D007659:Ketones / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
D000577:Amides; D015853:Cysteine Proteinase Inhibitors; D007202:Indicators and Reagents; D007659:Ketones