Graminaceous plants, when grown in iron-poor soil, produce and secrete low molecular weight iron-chelating compounds (phytosiderophores) for the sequestering and transport of iron to the plant itself. We continue to be interested in synthesizing avenic acid (the phytosiderophore produced by oats) and related analogs in order to study this iron-transport system. A key approach of our current synthesis of avenic acid utilized a convenient advanced intermediate to which we strategically reduced its terminal aspartic acid segment providing a homoserine equivalent required for the avenic acid “backbone”. Subsequent functional group transformations gave avenic acid in good overall yield.

Convenient and relatively efficient total synthesis of avenic acid

254th National Meeting (2017)

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