A PRACTICAL SYNTHESIS OF (1S,2R)-1-AMINO-2-INDANOL, A KEY COMPONENT OF HIV PROTEASE INHIBITOR, INDINAVIR

The synthesis of (1S,2R)-1-amino-2-indanol, a key component of HIV pro tease inhibitor, is accomplished in eight steps from D-phenylalanine. The starting material is converted into 2-acetoxy-1-indanone in four s teps involving intramolecular Friedel-Crafts cyclization. The stereoch emically labile alpha-acetoxy ketone is hydrolyzed to 2-hydroxy-1-inda none using a catalytic amount of scandium triflate without any loss of the optical purity. Diastereoselective hydrogenation of alpha-hydroxy oxime, derived from the alpha-hydroxy ketone, gives the amino alcohol in 96% cis-selectivity. Optical purity of the starting material is pe rfectly retained throughout the transformations.