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 | |
| Publication status | Published - 9 Jul 2019 |
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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
M3 - Article
VL - 21
SP - 5519
EP - 5523
JO - Organic Letters
JF - Organic Letters
SN - 1523-7052
IS - 14
ER -