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A new approach to synthesis of b,a-amino hydroxy acids


b-Amino-a-hydroxy acids are both very important and very powerful intermediates as drug and drugs candidates. b-amino-a-hydroxy acids are the constituent of several natural products which possess biological activity. We describe a new method for the synthesis of the amino acids. The uniqueness of our strategy allow us to modify the functional groups, such as ester, hydroxyl, and carbonyl.

We start from a simple compound, methoxy furan, to form b-hydroxy ester stereoselectively by using the Reformatsky reaction. The employment of the Mitsunobu reaction to b-hydroxy ester derivative will lead the inversion of alcohol to the opposite stereoselectivity. The azidation under the Mitsunobu condition will form azido derivatives with the inversion of stereochemistry.

The oxydation of furan and the reduction of carbonyl group of oxidized furan will yield amino alcohol selectively. At the final stage, ozonolysis of the double bond will be cleaved to an aldehyde which will be oxidized to the b-amino-a-hydroxy amino acids.

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