Stereoselective total synthesis of all the stereoisomers of (+)- and (−)-febrifugine and halofuginone

Abstract

A convenient method for the total synthesis of all the stereoisomers of febrifugine and halofuginone using D-arabinose and L-arabinose as the key starting materials is reported. Apart from the inherent stereocenters in these pentose sugars, the method utilizes the selective hydrogenolysis of the anomeric O-benzyl group, stereoselective Grignard reaction and Wacker oxidation as the key steps to obtain the important precursors for the total synthesis.