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Total Synthesis of [13 C2 ]-Labeled Phytosiderophores of the Mugineic and Avenic Acid Families.

Journal of labelled compounds & radiopharmaceuticals(2023)

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Abstract
We, herein, report the synthesis of C-13(2)-labeled natural products from the mugineic acid and avenic acid family. These phytosiderophores ("plant iron carriers") are built up from non-proteinogenic amino acids and play a key role in micronutrient uptake in gramineous plants. In this work, two central building blocks are prepared from labeled starting materials (C-13(2)-bromoacetic acid, C-13(2)-glycine) and further employed in our recently reported divergent, branched synthetic strategy delivering eight isotopically labeled phytosiderophores. The required labeled building blocks (C-13(2)-l-allylglycine and a related hydroxylated derivative) were prepared via enantioselective phase-transfer catalysis and enantio- and diastereoselective aldol condensation with a chiral auxiliary, respectively, both potentially valuable themselves for other synthetic routes toward labeled (natural) products.
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Plant Signaling
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