Total synthesis of [13C2]-labelled phytosiderophores of the mugineic and avenic acid families

20 July 2023, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

We herein report the synthesis of 13C2-labelled 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 labelled starting materials (13C2-bromoacetic acid, 13C2-glycine) and further employed in our recently reported divergent, branched synthetic strategy delivering eight isotopically labelled phytosiderophores. The required labelled 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 towards labelled (natural) products.

Supplementary materials

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Supporting information Synthesis and Analysis
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Details of chemical synthesis and analysis of the compounds discussed in the manuscript
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