Synthesis of 6,7-dehydroartemisinic acid
Abstract
The natural product 6,7-dehydroartemisinic acid from Artemisia annua has been synthesized in four steps from artemisitene, which was in turn prepared in four steps from commercially available artemisinin. The forward synthesis involves the acid degradation of artemisitene and some comparisons are made between the products from this reaction and the more extensively studied acid degradation reaction of its 11,13-dihydro analogue, artemisinin.
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Artemisitene can be obtained readily by chemical transformations of artemisinin, and a partial synthesis of artemisitene from artemisinic acid (473) has been reported.
“although artemisitene can be obtained readily by chemical transformations of artemisinin [165,213,241,242]; and a partial synthesis of artemisitene from artemisinic acid (473) has also been reported [243].”
From The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao) (2010) · cites this paper as [165]
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Self-citation
- Authors
- Sy, L.-K., & Brown, G. D.
- Affiliations
- University of Hong Kong (HK)
- Corresponding author
- Brown, Geoffrey D.
- ORCID
- Brown, Geoffrey D.
- Venue
- Journal of the Chemical Society, Perkin Transactions 1
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2001
- Issue
- 19
- Pages
- 2421-2429
- ISSN
- 1364-5463 (ISSN-L)
- 1472-7781
- OpenAlex
- W2033248828
- Cited by
- 19
- References
- 29
- Citations by year
- 2025: 2 · 2022: 1 · 2016: 1
- FWCI
- 0.62
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the Chemical Society Perkin Transactions 1 (publishedVersion)
- The HKU Scholars Hub (University of Hong Kong) (submittedVersion)
- Funders
- University of Hong Kong
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biological Activity of Diterpenoids and Biflavonoids
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Keywords
- artemisinin, Artemisia annua, total synthesis, acid degradation, sesquiterpene lactones
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