Synthesis and Bioactivity of a Macrocidin B Stereoisomer

  • Org Lett. 2021 Nov 5;23(21):8273-8276. doi: 10.1021/acs.orglett.1c03013.
Stefanie E Weber  1 ,  Juliane Gaß  1 ,  Haoxuan Zeng  2 ,  Maike Erb-Brinkmann  3 ,  Rainer Schobert  1
Affiliations
  • 1. Organic Chemistry Laboratory, University of Bayreuth, Universitätsstrasse 30, 95440 Bayreuth, Germany.
  • 2. Department of Microbial Drugs, Helmholtz Centre for Infection Research GmbH, Inhoffenstrasse 7, 38124 Braunschweig, Germany.
  • 3. PHYTOsolution, Querfurter Strasse 9, 06632 Freyburg, Germany.
PMID: 34633201 DOI: 10.1021/acs.orglett.1c03013
Abstract

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.

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