Highly efficient chiral-pool synthesis of (2S,4R)-4-hydroxyornithine.
[reaction: see text] A concise synthesis of the amino acid (2S,4R)-4-hydroxyornithine is described. Starting from diprotected L-aspartic acid, the scaffold of the target compound is constructed in a three-step approach: an efficient alpha-nitroketone formation through acylation of nitromethane is followed by a diastereoselective reduction of the resulting ketone. In the last step, the nitro group is reduced to furnish the (2S,4R)-4-hydroxyornithine scaffold. This new approach to the title compound offers advantages to the synthetic pathways previously described.
Rudolph
J
J
Bayer AG, Central Research, Life Science, Building Q18, D-51368 Leverkusen, Germany. joachim.rudolph.b@bayer.com
Hannig
F
F
Theis
H
H
Wischnat
R
R
D001224:Aspartic Acid / Q000737:chemistry; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D013237:Stereoisomerism
C438930:4-hydroxyornithine; D001224:Aspartic Acid; D009952:Ornithine