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

Biswanath Das; Joydeep Banerjee; Nikhil Chowdhury; Anjoy Majhi

doi:10.1248/cpb.54.1725

Notes

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

Biswanath Das, Joydeep Banerjee, Nikhil Chowdhury, Anjoy Majhi

著者情報

キーワード: (E)-α-methylcinnamic acid, stereoselective synthesis, Baylis–Hillman adduct, hypolipidemic agent, LK-903

ジャーナルフリー

2006 年 54 巻 12 号 p. 1725-1727

DOI https://doi.org/10.1248/cpb.54.1725

詳細

抄録

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.

責任著者(Corresponding author)

J-STAGEへの登録はこちら（無料）