Synthesis of (+)- and (-)-statine via chiral sulfoxide chemistry

Statine ([3S,4S]-4-amino-3-hydroxy-6-methylheptanoic acid) is a nonproteinogenic amino acid contained in microbial aspartyl protease inhibitors such as Pepstatin. A number of syntheses of the four stereoisomers of statine has been reported. Extremely effective and highly stereoselective are the approaches of Rich (1988) with the modification of Reetz (1989), Noyori (1988), Terashima (1990), and Gennari (1995). Most of the conceivable retrosynthetic pathways to statine have been explored.