Highly efficient approach to orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine.
[reaction: see text] A concise stereoselective approach to both orthogonally protected (2S,4R)- and (2S,4S)-4-hydroxyornithine, key constituents of the biphenomycin- and clavalanine-type antibiotics, respectively, has been developed. The approach is based on bis(oxazoline) copper(II)-complex-catalyzed diastereoselective Henry reactions of nitromethane with the homoserine-derived aldehyde 6. The synthesis of this versatile chiral building block has been markedly improved.
Paintner
Franz F
FF
Department Pharmazie, Zentrum für Pharmaforschung, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus C, D-81377 München, Germany. franz.paintner@cup.uni-muenchen.de
Allmendinger
Lars
L
Bauschke
Gerd
G
Klemann
Patricia
P
D003300:Copper / Q000737:chemistry; D015394:Molecular Structure; D009952:Ornithine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
C438930:4-hydroxyornithine; D010080:Oxazoles; D003300:Copper; D009952:Ornithine