A modular synthetic approach toward exhaustively stereodiversified ligand libraries

This report describes a modular approach to the synthesis of stereodiversif ied natural product like libraries. Monomers 2 and 3 were coupled in parall el by silyl tethered olefin metathesis to generate all 16 stereoisomers of cis-enediols 1. All 16 stereoisomers were incorporated into chimerae having flanking peptidic segments. These chimerae exhibited a broad range of hydr ophobicities, raising the possibility that stereochemical variation might b e used to tune the pharmacologic properties of small molecules.