Stereocontrolled Synthesis and Biological Activity of two Diastereoisomers of the Potent HIV-1 Protease Inhibitor Saquinavir

A general enantioselective synthesis of new syn-hydroxyethylamine isosteres has been developed. The approach, based on the controlled opening of functionalized optically active 2,3-epoxy amines, can be conveniently used for the preparation of new peptidomimetics with various residues. Finally the total synthesis of two diastereoisomer analogues of HIV-Protease inhibitor Saquinavir has been achieved and their biological activity evaluated. (C) 2007 Elsevier Ltd. All rights reserved.