Synthesis and Bioactivity of a Macrocidin B Stereoisomer

A stereoisomer of macrocidin B, a presumed metabolite of the fungus Phoma macrostoma, was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was N-β-ketoacylated with a fully functionalized octanoyl Meldrum’s acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macro...

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Bibliographic Details
Published in:Organic letters 2021-11, Vol.23 (21), p.8273-8276
Main Authors: Weber, Stefanie E, Gaß, Juliane, Zeng, Haoxuan, Erb-Brinkmann, Maike, Schobert, Rainer
Format: Article
Language:English
Subjects:
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - pharmacology
Biofilms - drug effects
Microbial Sensitivity Tests
Molecular Structure
Staphylococcus aureus - drug effects
Stereoisomerism
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Summary:A stereoisomer of macrocidin B, a presumed metabolite of the fungus Phoma macrostoma, was synthesized in 18 steps and 2.7% yield from protected l-tyrosine that was N-β-ketoacylated with a fully functionalized octanoyl Meldrum’s acid. Dieckmann condensation gave a 3-acyltetramic acid, which was macrocyclized via Williamson etherification between the phenol and epi-bromohydrin termini. This macrocidin B stereoisomer showed a weaker herbicidal effect than macrocidin A and no similar inhibitory effect on biofilms of Staphylococcus aureus.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.1c03013