Graminaceous plants, when grown in iron-poor soil produce and secrete low molecular weight iron-chelating compounds (phytosiderophores) for the sequestering and active 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. (S)-3,4-Di-tert-butoxy-4-oxobutanoic acid is an important early precursor in the synthesis of avenic acid and closely related analogs we have been preparing. Our synthetic path leading to this necessary differentially protected L-malic acid has also yielded several other potentially synthetically useful differentially protected L-malic acids. We present our synthesis, optimization, and progress toward obtaining x-ray crystallography data of these differentially protected L-malic acids as well as their use in the total synthesis of avenic acid and selected avenic acid analogs.

Synthesis and optimization of differentially protected <i>L</i>-malic acid and avenic acid analogs

246th National Meeting (2013)

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Synthesis and optimization of differentially protected L-malic acid and avenic acid analogs