Total synthesis of the antimalarial ascidian natural product albopunctatone

Glenn A Pullella; Adam P Wdowiak; Melissa L Sykes; Leonardo Lucantoni; Kirill V Sukhoverkov; Bilal Zulfiqar; Alexandre N Sobolev; Nicholas P West; Joshua S Mylne; Vicky M Avery; Matthew J Piggott

doi:10.1021/acs.orglett.9b01838

Total synthesis of the antimalarial ascidian natural product albopunctatone

Glenn A Pullella, Adam P Wdowiak, Melissa L Sykes, Leonardo Lucantoni, Kirill V Sukhoverkov, Bilal Zulfiqar, Alexandre N Sobolev, Nicholas P West, Joshua S Mylne, Vicky M Avery, Matthew J Piggott

Research output: Contribution to journal › Article

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.

Original language	English
Pages (from-to)	5519-5523
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.9b01838
Publication status	Published - 9 Jul 2019

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Pullella, G. A., Wdowiak, A. P., Sykes, M. L., Lucantoni, L., Sukhoverkov, K. V., Zulfiqar, B., ... Piggott, M. J. (2019). Total synthesis of the antimalarial ascidian natural product albopunctatone. Organic Letters, 21(14), 5519-5523. https://doi.org/10.1021/acs.orglett.9b01838

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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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year = "2019",

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doi = "10.1021/acs.orglett.9b01838",

language = "English",

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pages = "5519--5523",

journal = "Organic Letters",

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Total synthesis of the antimalarial ascidian natural product albopunctatone. / Pullella, Glenn A; Wdowiak, Adam P; Sykes, Melissa L; Lucantoni, Leonardo; Sukhoverkov, Kirill V; Zulfiqar, Bilal; Sobolev, Alexandre N; West, Nicholas P; Mylne, Joshua S; Avery, Vicky M; Piggott, Matthew J.

In: Organic Letters, Vol. 21, No. 14, 09.07.2019, p. 5519-5523.

Research output: Contribution to journal › Article

TY - JOUR

T1 - Total synthesis of the antimalarial ascidian natural product albopunctatone

AU - Pullella, Glenn A

AU - Wdowiak, Adam P

AU - Sykes, Melissa L

AU - Lucantoni, Leonardo

AU - Sukhoverkov, Kirill V

AU - Zulfiqar, Bilal

AU - Sobolev, Alexandre N

AU - West, Nicholas P

AU - Mylne, Joshua S

AU - Avery, Vicky M

AU - Piggott, Matthew J

PY - 2019/7/9

Y1 - 2019/7/9

N2 - 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.

AB - 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.

U2 - 10.1021/acs.orglett.9b01838

DO - 10.1021/acs.orglett.9b01838

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10.1021/acs.orglett.9b01838