Synthesis of Orthogonally Protected S,S-2,6-Diaminopimelic Acid via Olefin Cross-Metathesis

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.

Keywords:

• Cross-metathesis
• diaminopimelic acid
• Grubbs catalyst