title: 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.
abstract: 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.
authors.affiliation: Organic Chemistry Division-I, Indian Institute of Chemical Technology. biswanathdas@yahoo.com
authors.forename: Biswanath
authors.initials: B
authors.lastname: Das
authors.forename: Joydeep
authors.initials: J
authors.lastname: Banerjee
authors.forename: Nikhil
authors.initials: N
authors.lastname: Chowdhury
authors.forename: Anjoy
authors.initials: A
authors.lastname: Majhi
mesh_terms: D002934:Cinnamates / Q000138:chemical synthesis*; D005989:Glycerides / Q000138:chemical synthesis*; D000960:Hypolipidemic Agents / Q000138:chemical synthesis; D015394:Molecular Structure
chemical_list: D002934:Cinnamates; D005989:Glycerides; D000960:Hypolipidemic Agents; C017974:methyl-p-myristyloxycinnamic acid 1-monoglyceride