Kratena, N., Gökler, T., Maltrovsky, L., Oburger, E., & Stanetty, C. (2020). A Unified Approach to Phytosiderophore Natural Products. Chemistry - A European Journal, 27(2), 577–580. https://doi.org/10.1002/chem.202004004
General Chemistry; Catalysis; Organic Chemistry; natural products; total synthesis; phytosiderophores
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Abstract:
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.
