Synthetic Applications of Baylis–Hillman Chemistry: An Efficient and Solely Stereoselective Synthesis of (E)-α-Methylcinnamic Acids and Potent Hypolipidemic Agent LK-903 from Unmodified Baylis–Hillman Adducts

Abstract

An efficient and solely stereoselective synthesis of (E)-α-methylcinnamic acids has been accomplished in single pot by reduction of the unmodified Baylis–Hillman adducts, methyl-3-hydroxy-3-aryl-2-methylenepropanoates with I₂/NaBH₄ reagent system at room temperature followed by hydrolysis. The efficacy of this method has been proved in the total synthesis of 1-[p-(myristyloxy)-α-methylcinnamoyl]glycerol, LK-903, a highly active hypolipidemic agent.