Practical conversion of artemisinic acid in desoxyartemisinin
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ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPractical conversion of artemisinic acid in desoxyartemisininMankil Jung, Hala N. ElSohly, Edward M. Croom, Andrew T. McPhail, and Donald R. McPhailCite this: J. Org. Chem. 1986, 51, 26, 5417–5419Publication Date (Print):December 1, 1986Publication History Published online1 May 2002Published inissue 1 December 1986https://pubs.acs.org/doi/10.1021/jo00376a070https://doi.org/10.1021/jo00376a070research-articleACS PublicationsRequest reuse permissionsArticle Views567Altmetric-Citations51LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-AlertscloseSupporting Info (1)»Supporting Information Supporting Information Get e-Alerts
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Photooxygenation of artemisinic acid (473) in vitro leads to arteannuin B (462) and 11,13-dehydro analogues of artemisinin.
“There is indeed ample precedent for the formation of such hydroperoxides from 473 by photooxygenation reactions in vitro [243], which lead both to arteannuin B (462) [251] and 11,13-dehydro analogues of artemisinin [254,308].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [254]
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 [254]
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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.”
BackgroundMethodAn efficient synthesis of qinghaosu and deoxoginghaosu from arteannuic acid
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“All the protons and carbons of the compound 4 were assigned by the analysis of its 1H, 13C, DEPT and HMBC, NMR spectra and compared with spectral data reported for artemisinic acid (You-You et al. 1982; Jung et al. 1986).”
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- Authors
- Jung, M., ElSohly, H. N., Croom, E. M., McPhail, A. T., & McPhail, D. R.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 1986-12
- Volume
- 51
- Issue
- 26
- Pages
- 5417-5419
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2089167334
- Cited by
- 58
- References
- 0
- Citations by year
- 2024: 2 · 2023: 1 · 2021: 2 · 2019: 3 · 2017: 2 · 2015: 1 · 2014: 2 · 2013: 2 · 2012: 1
- FWCI
- 2.71
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- The Journal of Organic Chemistry (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Phytochemical compounds biological activities
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Keywords
- artemisinic acid, sesquiterpene lactones, total synthesis, antimalarial compounds
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