Syntheses of Cytosporones A, C, J, K, and N, Metabolites from Medicinal Fungi

Andrew M. Beekman, Russell A. Barrow

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Abstract

The syntheses of the fungal metabolites cytosporones A, (±)-C, and N are reported. And the syntheses of cytosporones J and K are described for the first time. The preparation of racemic cytosporone J and racemic cytosporone K, natural products containing the rare 3-isochromanone substructure, was achieved in 8 linear steps with an overall yield of 45 % and 7 linear steps in 46 % yield, respectively, resulting in the complete characterization of these compounds for the first time. The key steps included a recently described homologation of benzoic acid to the analogous phenyl acetate using Birch reductive alkylation conditions, acylation of the appropriate phenyl acetate derivative, and a selective reduction and spontaneous biomimetic lactonization to yield the 3-isochromanone skeleton. The synthesized natural products were evaluated for their biological activity against several clinical strains of human pathogens with all compounds displaying weak antimicrobial activity.
Original languageEnglish
Pages (from-to)1583-1592
Number of pages10
JournalAustralian Journal of Chemistry
Volume68
Issue number10
DOIs
Publication statusPublished - 5 Jun 2015

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