Journal
CHEM
Volume 6, Issue 5, Pages 1183-1189Publisher
CELL PRESS
DOI: 10.1016/j.chempr.2020.04.007
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Funding
- University of Vienna
- Austrian Science Fund (FWF) [W1232]
- Austrian Academy of Sciences
- FWF
- Austrian Science Fund (FWF) [W1232] Funding Source: Austrian Science Fund (FWF)
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Although clinical applications of abundant feedstock triterpenoids such as oleanolic acid are limited because of poor solubility and bioavailability, synthetic access to higher hydroxylated oleanane terpenoids is challenging. We now report the use of relay C-H oxidation logic to mimic the processes carried out in nature by P450 monooxygenase enzymes. To this end, we used the C-23-OH as natural handle for a hydrogen-atom transfer to access C-6, enabling the first syntheses of highly oxidized natural products uncargenin C and protobassic acid as well as uncovering the anti-leukemic activity of a synthetic intermediate.
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