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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
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: | 25 Sep 2024 12:33 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/62961 |
| DOI: | 10.1071/CH15144 |
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