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 |
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Authors: | Das Biswanath Banerjee Joydeep Chowdhury Nikhil Majhi Anjoy |
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Institution: | Organic Chemistry Division-I, Indian Institute of Chemical Technology. biswanathdas@yahoo.com |
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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. |
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