Institute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9, 1060, Vienna, Austria.
Institute of Soil Research, BOKU Vienna, Konrad-Lorenz-Strasse 24, 3430, Tulln, Austria.
Chemistry. 2021 Jan 7;27(2):577-580. doi: 10.1002/chem.202004004. Epub 2020 Oct 28.
This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative "east-to-west" 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 (l-malic 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.
这项工作报道了 8 种 mugineic 酸和 avenic 酸族天然产物（植物铁载体）的简洁全合成。一种创新的“从东到西”的三聚体产物的组装导致了高度的发散，使得每个最终产物仅通过 10 或 11 步反应即可形成，整体合成工作量最小。手性池起始原料（l-苹果酸、苏氨酸）用于外部分子砌块，而中间分子砌块则通过非对映和对映选择性方法获得。这项工作的一个亮点是直接制备差向异构体羟氮杂环丁烷氨基酸，这些氨基酸本身就是有用的构建块，使得 3''-羟基 mugineic 酸和 3''-羟基-2'-脱氧 mugineic 酸的首次合成成为可能。
