Tetrahedron

Total synthesis of mugineic acid. Efficient use of the phenyl group as the carboxyl synthon

F Matsuura, Y Hamada, T Shioiri

Index: Matsuura, Fumiyoshi; Hamada, Yasumasa; Shioiri, Takayuki Tetrahedron, 1993 , vol. 49, # 36 p. 8211 - 8222

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Citation Number: 32

Abstract

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.