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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.

Citation

Stefanie E Weber, Juliane Gaß, Haoxuan Zeng, Maike Erb-Brinkmann, Rainer Schobert. Synthesis and Bioactivity of a Macrocidin B Stereoisomer. Organic letters. 2021 Nov 05;23(21):8273-8276

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PMID: 34633201

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