A stereo-controlled synthesis of 2,4-dimethyl-4-hydroxy-16-PHENYLHEXADECANOIC ACID (cas 19629-78-8) 1,4-lactone and its PPAR activities

Add time:08/29/2019    Source:sciencedirect.com

A novel class of natural PPAR agonists, 2,4-dimethyl-4-hydroxy-16-phenylhexadecanoic acid 1,4-lactone (1), were discovered in marine natural product libraries. The synthesis of 1 was accomplished starting from vinylmethyl ketone. Ring formation of the α,γ dialkyl γ-lactone was achieved via the stereo-controlled reaction of a ketyl radical anion with a chiral methacrylate. In the PPAR agonistic assay, the most potent of the four stereoisomers had EC50 values of 12 μM for mPPARα, 9 μM for mPPARδ and >100 μM for mPPARγ.

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