Affiliation:
1. Institute of Applied Synthetic Chemistry, TU Wien Vienna Austria
2. Institute of Soil Research, BOKU Vienna Tulln Austria
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.
Subject
Organic Chemistry,Spectroscopy,Drug Discovery,Radiology, Nuclear Medicine and imaging,Biochemistry,Analytical Chemistry
Cited by
1 articles.
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