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

Andrew M. Beekman; Russell A. Barrow

doi:10.1071/CH15144

RESEARCH ARTICLE

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

Andrew M. Beekman ^A and Russell A. Barrow ^A ^B

+ Author Affiliations

- Author Affiliations

^A Research School of Chemistry, Australian National University, Acton, ACT, 2601, Australia.

^B Corresponding author. Email: rab@anu.edu.au

Australian Journal of Chemistry 68(10) 1583-1592 https://doi.org/10.1071/CH15144
Submitted: 23 March 2015 Accepted: 24 April 2015 Published: 5 June 2015

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.

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

Abstract

References

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