Synthesis of Orthogonally Protected<i>S,S</i>-2,6-Diaminopimelic Acid via Olefin Cross-Metathesis

Abstract

Abstract A short synthesis of orthogonally protected S,S-diaminopimelic acid, DAP, via a selective cross-metathesis between S-allyl glycine and S-vinyl glycine followed by hydrogenation is reported. By analogy, the S,S-diaminosuberic acid, DAS, is produced by self-metathesis of S-allyl glycine, and the self-metathesis of S-vinyl glycine is described.