Journal
ORGANIC LETTERS
Volume 23, Issue 21, Pages 8273-8276Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c03013
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Funding
- German Bundesministerium fur Wirtschaft und Energie [ZF4514501MD7, ZF4513301MD7]
- Ministry for Science & Culture of the German State of Lower Saxony [MWK 21-78904-63-5/19]
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In this study, a stereoisomer of macrocidin B was synthesized, showing a weaker herbicidal effect compared to macrocidin A and no similar inhibitory effect on biofilms of Staphylococcus aureus.
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-beta-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.
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