Straightforward and Diastereoselective Synthesis of Tetrafunctionalized Thiol Synthons for the Design of Metallopeptidase Inhibitors

Tetrafunctionalized thiol-containing synthons with different side-chains have been prepared with good yields by a straightforward diastereoselective and general methodology. The key step of the synthesis consisted of a tandem reduction and Wittig–Horner reaction, which conserved the stereochemistry of the starting material. The method was generalized to different side-chains, allowing synthons for designing inhibitors of various classes of zinc metallopeptidases to be easily obtained.