An efficient synthesis of qinghaosu and deoxoginghaosu from arteannuic acid
Abstract
Photo-oxidation of cyclic enol ether (3) and successive treatments with trimethylsilyl trifluoromethanesuiphonate (TfOTMS) afforded three compounds, deoxoginghaosu (4), (5), and (6); oxidation of (4) with RuO4 gave qinghaosu (1).
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The step iii reaction most probably proceeds via an ene-type mechanism similar to the conversion of 480 to 481, apparently without requirement for light, with 3O2 rather than 1O2 as the active species.
“This reaction most probably proceeds via an “ene-type” mechanism similar to that for the conversion of 480 to 481, although apparently without the requirement for light (i.e. 3O2 rather than 1O2 is perhaps the active species) [193,236,304,305].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [236]
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 [236]
Chemical synthesis of artemisinin is far too expensive for many in the Third World because of the structural complexity of the target and the large number of steps in published synthetic routes.
“Although artemisinin can be produced by chemical synthesis [171,228,229,230,231,232,233,234,235,236,237,238,239], the structural complexity of this target and the large number of steps involved in all published synthetic routes render this approach far too expensive for many in the Third World who are most affected by malaria.”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [236]
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- Authors
- Ye, B., & Wu, Y.-L.
- ORCID
- Wu, Yu-Lin
- Venue
- Journal of the Chemical Society, Chemical Communications
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1990
- Issue
- 10
- Pages
- 726
- ISSN
- 0022-4936 (ISSN-L)
- OpenAlex
- W2058238262
- Cited by
- 46
- References
- 12
- Citations by year
- 2024: 1 · 2023: 2 · 2021: 1 · 2020: 1 · 2018: 2 · 2017: 2 · 2013: 1 · 2012: 3
- FWCI
- 0.70
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the Chemical Society Chemical Communications (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biological Activity of Diterpenoids and Biflavonoids
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Keywords
- artemisinin, photooxidation, cyclic enol ethers, trimethylsilyl trifluoromethanesulfonate, ruthenium tetroxide oxidation, total synthesis, artemisinin derivatives
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