Total Synthesis of Mugineic Acid. Efficient Use of the Phenyl Group as the Carboxyl Synthon

Article abstract of DOI:10.1016/S0040-4020(01)88039-X

Stereoselective total synthesis of mugineic acid (1), a unique phytosiderophore from roots of barley, has been achieved from readily available (2S,3S)- and (2R,3R)-2,3-epoxycinnamyl alcohols (5) and (6).The key step is the oxidation of the phenyl group to the carboxylic acid by use of the ruthenium trichloride-sodium metaperiodate system.