A facile semisynthesis of the antimalarial drug qinghaosu
Abstract
Semisynthesis of the antimalarial drug.
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The evidence for steps ii)-iv) proposed in Scheme 12 comes solely from in vitro studies conducted with the tertiary allylic hydroperoxide 481.
“The evidence for steps ii)-iv) which are proposed in Scheme 12 comes solely from in vitro studies, conducted with the tertiary allylic hydroperoxide 481 [171,236,237,239,254], which can be obtained in good yield from photosensitized oxygenation of 480 [193,218].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [237]
The semi-synthesis of artemisinin from microbially-produced artemisinic acid requires two further chemical steps: reduction of the exocyclic double bond and photo-sensitized oxidation of the endocyclic double bond to produce the 1,2,4-trioxane ring.
“The semi-synthesis of artemisinin (495) from microbially-produced artemisinic acid (473) then requires two further chemical steps: reduction of the exocyclic double bond; and photo-sensitized oxidation of the endocyclic double bond to produce the 1,2,4-trioxane ring in (495) [156,237].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [237]
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“Roth and Acton proposed a conversion of artemisinic acid into artemisinin with a 30% yield [69].”
BackgroundA total synthesis of the antimarial natural product (+)-qinghaosu
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“In addition, NaBH4/NiCl2 [59] (98% yield) and LiBH4/NiCl2 [60] (quantitative yield) were used for the reduction of artemisinic acid.”
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Radical chemistry of artemisinin
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Artemisinin: An Endoperoxidic Antimalarial from Artemisia annua L.
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“Finally, a series of condensation reactions generate the three missing rings of artemisinin (Vonwiller et al., 1995; Reiling et al., 2006; Roth and Acton, 1991; Constantino et al., 1996).”
BackgroundSynthesis of a Novel Artemisinin Analogue Having Potent Antimalarial Activity
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“Simplified semi-synthetic path from dihydroartemisinic acid (DHAA) to artemisinin (ART) based on Acton and Roth [9–11] with the singlet oxygen formed by a photo-induced process (PS: photosensitizer). dynamics in complex synthesis processes for finally designing the process, mathematical modeling…”
- Authors
- Roth, R. J., & Acton, N.
- Venue
- Journal of Chemical Education
- Publisher
- American Chemical Society (ACS)
- Published
- 1991-07
- Volume
- 68
- Issue
- 7
- Pages
- 612
- ISSN
- 0021-9584 (ISSN-L)
- 1938-1328
- OpenAlex
- W2052075786
- Cited by
- 41
- References
- 0
- Citations by year
- 2025: 1 · 2024: 2 · 2023: 1 · 2018: 2 · 2017: 2 · 2014: 1 · 2013: 1 · 2012: 4
- FWCI
- 0.26
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of Chemical Education (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical compounds biological activities
- Health Sciences › Medicine › Public Health, Environmental and Occupational Health › Malaria Research and Control
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Keywords
- artemisinin, semisynthesis, antimalarial drugs
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