Synthetic applications of Baylis-Hillman chemistry: an efficient and solely stereoselective synthesis of (E)-alpha-methylcinnamic acids and potent hypolipidemic agent LK-903 from unmodified Baylis-Hillman adducts.
An efficient and solely stereoselective synthesis of (E)-alpha-methylcinnamic acids has been accomplished in single pot by reduction of the unmodified Baylis-Hillman adducts, methyl-3-hydroxy-3-aryl-2-methylenepropanoates with I(2)/NaBH(4) reagent system at room temperature followed by hydrolysis. The efficacy of this method has been proved in the total synthesis of 1-[p-(myristyloxy)-alpha-methylcinnamoyl]glycerol, LK-903, a highly active hypolipidemic agent.
Das
Biswanath
B
Organic Chemistry Division-I, Indian Institute of Chemical Technology. biswanathdas@yahoo.com
Banerjee
Joydeep
J
Chowdhury
Nikhil
N
Majhi
Anjoy
A
D002934:Cinnamates / Q000138:chemical synthesis*; D005989:Glycerides / Q000138:chemical synthesis*; D000960:Hypolipidemic Agents / Q000138:chemical synthesis; D015394:Molecular Structure
D002934:Cinnamates; D005989:Glycerides; D000960:Hypolipidemic Agents; C017974:methyl-p-myristyloxycinnamic acid 1-monoglyceride