A concise synthesis of protected (2S,4R)-4-hydroxyornithine

A short synthesis of the nonproteinogenic amino acid, (2S,4R)-4-hydroxyornithine is described. Starting from racemic benzyl glycidol, the scaffold of the target compound was constructed in high enantio- and diastereoselectivity using Jacobsen's hydrolytic kinetic resolution (HKR) and regioselective opening of an epoxide as key steps. (c) 2008 Elsevier Ltd. All rights reserved.