Application of the Dakin-West reaction for the synthesis of oxazole-containing dual PPARalpha/gamma agonists.
An improved method for the preparation of a series of oxazole-containing dual PPARalpha/gamma agonists is described. A synthetic sequence utilizing a Dakin-West reaction was devised that allows for the introduction of the oxazole ring either late in the synthetic sequence via aminomalonate-derived chemistry or in pivotal SAR intermediates derived from aspartic acid.
Godfrey
Alexander G
AG
Lilly Research Laboratories, Eli Lilly & Company, Lilly Corporate Center, Indianapolis, Indiana 46285, USA. agg@lilly.com
Brooks
Dawn A
DA
Hay
Lynne A
LA
Peters
Mary
M
McCarthy
James R
JR
Mitchell
David
D
D001224:Aspartic Acid / Q000031:analogs & derivatives / Q000737:chemistry; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis*; D018160:Receptors, Cytoplasmic and Nuclear / Q000819:agonists*; D014157:Transcription Factors / Q000819:agonists*
D007202:Indicators and Reagents; D010080:Oxazoles; D018160:Receptors, Cytoplasmic and Nuclear; D014157:Transcription Factors; D001224:Aspartic Acid