Stereocontrolled synthesis of the PPAR-gamma agonist 10-nitrolinoleic acid.
The naturally occurring PPAR-gamma ligand 10-nitrooctadeca-9(E),12(Z)-dienoic acid (10-nitrolinoleic acid) (2a) was prepared as a single regio- and geometrical isomer in a practical eight-step, convergent sequence. The synthetic route featured a nitro aldol reaction between 9-oxononanoic acid methyl ester (3) and 1-nitronon-3(Z)-ene (4) in the key carbon-carbon bond forming step. The ability of 2a (and its methyl ester 9) to bind to PPAR-gamma in a ligand-binding assay is reported.
Dunny
Elizabeth
E
Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland.
Evans
Paul
P
D002851:Chromatography, High Pressure Liquid; D008041:Linoleic Acids / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009574:Nitro Compounds / Q000737:chemistry* / Q000494:pharmacology; D047495:PPAR gamma / Q000819:agonists*; D013237:Stereoisomerism
C501855:10-nitro-9,12-octadecadienoic acid; D008041:Linoleic Acids; D009574:Nitro Compounds; D047495:PPAR gamma