Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl)serine as potential in vivo precursors of fluorinated norepinephrines.
The title compounds were prepared by the aldol condensation of 3,4-dibenzyloxy-2-fluorobenzaldehyde and 4,5-dibenzyloxy-2-fluorobenzaldehyde with the oxazolidinone 2, a chiral glycine equivalent. Removal of the chiral auxiliary and blocking groups produced the target amino acids 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl)serine (1b and 1c) in >98% ee.
Herbert
B
B
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda, Maryland 20892, USA.
Kim
I H
IH
Kirk
K L
KL
D000322:Adrenergic Agonists / Q000138:chemical synthesis; D015103:Droxidopa / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005461:Fluorine / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009638:Norepinephrine / Q000031:analogs & derivatives* / Q000096:biosynthesis; D013237:Stereoisomerism
D000322:Adrenergic Agonists; D005461:Fluorine; D015103:Droxidopa; D009638:Norepinephrine