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

Beekman, Andrew M. ORCID: https://orcid.org/0000-0002-3056-6406 and Barrow, Russell A. (2015) Syntheses of Cytosporones A, C, J, K, and N, Metabolites from Medicinal Fungi. Australian Journal of Chemistry, 68 (10). pp. 1583-1592. ISSN 0004-9425

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Depositing User: Pure Connector
Date Deposited: 15 Mar 2017 01:40
Last Modified: 01 Oct 2022 02:08
URI: https://ueaeprints.uea.ac.uk/id/eprint/62961
DOI: 10.1071/CH15144

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