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- Title
Total synthesis of [<sup>13</sup>C<sub>2</sub>]‐labeled phytosiderophores of the mugineic and avenic acid families.
- Authors
Kratena, Nicolas; Draskovits, Markus; Biedermann, Nina; Oburger, Eva; Stanetty, Christian
- Abstract
We, herein, report the synthesis of 13C2‐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 (13C2‐bromoacetic acid, 13C2‐glycine) and further employed in our recently reported divergent, branched synthetic strategy delivering eight isotopically labeled phytosiderophores. The required labeled building blocks (13C2‐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.
- Subjects
PHASE-transfer catalysis; ENANTIOSELECTIVE catalysis; ALDOL condensation; IRON; NATURAL products; ECO-labeling
- Publication
Journal of Labelled Compounds & Radiopharmaceuticals, 2023, Vol 66, Issue 13, p428
- ISSN
0362-4803
- Publication type
Article
- DOI
10.1002/jlcr.4064