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

Beekman, Andrew M. 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 (former - to 2024)
UEA Research Groups:	Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
Depositing User:	Pure Connector
Date Deposited:	15 Mar 2017 01:40
Last Modified:	28 Mar 2025 07:59
URI:	https://ueaeprints.uea.ac.uk/id/eprint/62961
DOI:	10.1071/CH15144

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