NOVEL PEPTIDE ISOSTERES THAT WERE DESIGNED TO INHIBIT THE BINDING OF THE HIV SURFACE GLYCOPROTEIN (GP120) TO THE T-CELL SURFACE GLYCOPROTEIN CD4

The cis- and trans-isomers of rop-1'-enyl]-N-methoxycarbonylcarbonylpy rrolidines have been prepared from a Wittig reaction between (S)-N-Boc -prolinal and the phosphorus ylide from RS)-3-iodo-2-benzyl-1-triisopr opylsilyloxypropane. In addition, o-3'-benzyl-3'-benzyloxycarbonylprop yl]pyrrolidine was prepared from the cis-alkene produced in the Wittig reaction. These were intended as peptide isosteres of the known inhib itors of HIV-lymphocyte binding N-methoxycarbonylcarbonylprolylphenyla lanyl benzyl esters, but did not possess such activity.