An efficient enantioselective synthesis of (S)-(-)-acromelobic acid.
[reaction: see text] A highly efficient enantioselective synthesis of (S)-(-)-acromelobic acid (1) was achieved via asymmetric hydrogenation of dehydroamino acid derivative (3) using (R,R)-[Rh(DIPAMP)(COD)]BF(4) catalyst followed by removal of protective groups in >98% ee and good over all yield. The key intermediate (3) was prepared from the commercially available citrazinic acid (4) in six steps.
Adamczyk
M
M
Department of Chemistry (9NM), Building AP20, Diagnostics Division, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, Illinois 60064-6016, USA. maciej.adamczyk@abbott.com
Akireddy
S R
SR
Reddy
R E
RE
D000409:Alanine / Q000031:analogs & derivatives* / Q000737:chemistry; D001487:Basidiomycota; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D007202:Indicators and Reagents; D011725:Pyridines; C416724:acromelobic acid; D000409:Alanine