Moiramide B

Moiramide B and andrimid are secondary metabolites originating from Gram-negative bacteria. Komura et al. described the first isolation of andrimid from Enterobacter sp. Later, Andersen et al. isolated andrimid together with moiramides A–C from Pseudomonas fluorescens, with andrimid and moiramide B showing potent in vivo antibiotic activity.

  • A. Fredenhagen, S. Y. Tamura, P. T. M. Kenny, H. Komura, Y. Naya, K. Nakanishi, J. Am. Chem. Soc. 1987, 109, 4409–4411.
  • Needham, M. T. Kelly, M. Ishige, R. J. Andersen, J. Org. Chem. 1994, 59, 2058–2063
  • M. P. Singh, M. J. Mroczenski-Wildey, D. A. Steinberg, R. J. Andersen, W. M. Maiese, M. Greenstein, J. Antibiot. 1997, 50, 270–273.

Moiramide B was synthesized via a Pd-cytalyzed allylic alkylation approach as a key step. An allylic side chain was introduced onto a chiral γ-amino-β-ketoamide. Subsequent ozonolysis and oxidation generated the succinimide motive.

  • C. Prudel, U. Kazmaier, "Total Synthesis of Moiramide B using an Allylic Alkylation Approach", Synlett 2024, in press. DOI: 10.1055/s-0042-1751578