A Unified Approach to Phytosiderophore Natural Products

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.

Automated summary

This study presents a concise total synthesis of eight natural products of the mugineic acid and avenic acid families using an innovative assembly approach, resulting in a high degree of divergence and minimal synthetic effort. Chiral pool starting materials and diastereo- and enantioselective methods were utilized to access key building blocks, allowing for the successful preparation of epimeric hydroxyazetidine amino acids and the synthesis of specific target products.