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A Unified Approach to Phytosiderophore Natural Products.

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-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.

SUBMITTER: Kratena N

PROVIDER: S-EPMC7821100 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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A Unified Approach to Phytosiderophore Natural Products.

Kratena Nicolas N Gökler Tobias T Maltrovsky Lara L Oburger Eva E Stanetty Christian C

Chemistry (Weinheim an der Bergstrasse, Germany) 20201028 2

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 wer ...[more]

PMID: 32897577

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