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Org Lett. 2019 Jul 19;21(14):5519-5523. doi: 10.1021/acs.orglett.9b01838. Epub 2019 Jul 9.

Total Synthesis of the Antimalarial Ascidian Natural Product Albopunctatone.

Author information

1
Discovery Biology, Griffith Institute for Drug Discovery , Griffith University , Nathan , Queensland , Australia.
2
Tuberculosis Research Laboratory, School of Chemistry and Molecular Biosciences , University of Queensland , Brisbane , Australia.

Abstract

The first approaches to the 10'-anthronyl-2-anthraquinone skeleton have been devised, allowing two syntheses of the marine natural product albopunctatone. Both routes involve regioselective addition of a nucleophilic masked anthraquinone to a protected chrysazin derivative; the best affords albopunctatone in five steps and 35% overall yield. Albopunctatone exhibits potent inhibitory activity against Plasmodium falciparum and negligible toxicity to a range of other microbial pathogens and mammalian cells.

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