NEW APPLICATIONS OF FLUORINATED BUILDING-BLOCKS

A new and versatile synthesis of optically active alpha-fluoromalonami de derivatives from enantiomerically pure 3-fluoro-2-azetidinones is d escribed. A fluorinated retroamide isostere based on these alpha-fluor omalonamides was introduced into a small peptidomimetic for use as an HIV-1 protease inhibitor. The same strategy was employed in efforts to prepare a novel trifluorostatone-type peptidomimetic.