[Zurück]

N. Kratena, T. Gökler, L. Maltrovsky, E. Oburger, C. Stanetty:
"A Unified Approach to Phytosiderophore Natural Products";
Chemistry - A European Journal, 26 (2020).

This work reports on the concise total synthesis
of eight natural products of the mugineic acid and avenic
acid families (phytosiderophores). An innovative "east-towest"
assembly of the trimeric products resulted in a high
degree of divergence enabling the formation of the final
products in just 10 or 11 steps each with a minimum of
overall synthetic effort. Chiral pool starting materials (lmalic
acid, threonines) were employed for the outer building
blocks while the middle building blocks were accessed
by diastereo- and enantioselective methods. A highlight
of this work consists in the straightforward preparation of
epimeric hydroxyazetidine amino acids, useful building
blocks on their own, enabling the first synthesis of 3´´-hydroxymugineic acid and 3´´-hydroxy-2´-deoxymugineic acid.

total synthesis, natural products, phytosiderophores

http://dx.doi.org/10.1002/chem.202004004

https://publik.tuwien.ac.at/files/publik_290956.pdf