Total synthesis of arteannuin (Quinghaosu) and related compounds
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Conference International Symposium on Organic Chemistry of Medicinal Natural Products, Shanghai, China, 1985-11-10–1985-11-14 Published Online: 2009-01-01 Published in Print: 1986-01-01 © 2013 Walter de Gruyter GmbH, Berlin/Boston
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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 [171]
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 [171]
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Cites
8th International Symposium on the Chemistry of Natural Products
(1972) · Zeitschrift für Chemie · doi:10.1002/zfch.19720120722 · Cited by 48 · see citing works
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Research works printed but not linked: 21
- a. Liu Jing-ming, Ni Mu-yun, Fan Ju-fen, Tu You-you, Wu Zhao-hau, Wu Yu-lin and Zhou Wei-shan, Acta Chimica Sinica, 37, 129 (1979);
- Tu You-you, Ni Mu-yun, Zhong yu-rong, Li Lan-na, Cui Shu-lian, Zhang Mu-qun, Wang Xiu-zhen and Liang Xiao-tian, Acta Pharmaceutica Sinica, 16, 366 (1981).
- Tu You-you, Ni Mu-yun and Liu Jing-ming, Planta Medica, 44, 143 (1982).
- Wu Zhao-hua and Wang Yan-yan, Acta Chimica Sinica, 42, 596 (1984).
- D. Jeremic, A. Jokic, A. Behbud and M. Stefanovic, Tetrahedron Letters 3039 (1973)
- Institute of Biophysics, Academia Sinica, Scientia Sinica, 22, 1114 (1979).
- Xu Xing-xiang, Wu Zhao-hua, Shen Ji-ming, Cheng Chao-huan, Wu Yu-lin and Zhou Wei-shan, Kexue Tongbao, 26, 947 (1981); Acta Chimica Sinica, 42, 333 (1984).
- Li Ying, Yu Pei-lin, Chen yi-xin, Li Liang-quan, Gai Yuan-zhu, Wang De-sheng and Zheng Ya-ping, Acta Pharmaceutica Sinica, 16, 429 (1981);
- Li Ying, Yu Pei-lin, Chen Yi-xin, and Ji Ru-yun, Acta Chimica Sinica, 40, 557(1982).
- Xu Xing-xiang, Zhu Jie, Huang Da-zhong and Zhou Wei-shan, Acta Chimica Sinica, 41,574 (1983); Acta Chimica Sinica,(English Edition) 98 (1983).
- Xu Xing-xiang, Zhu Jie, Huang Da-zhong and Zhou Wei-shan, Acta Chimica Sinica, 42, 940 (1984).
- G. Schmid, W. Hofheinz, J.Amer. Chem. Soc. 105, 624 (1983).
- H. J. C. Jacobs, F. Havinga, Tetrahedron, 28, 135 (1972).
- Zhou Wei-shan, Zhang Jing-li and Wu Zhao-hua, Acta Chimica Sinica, 42, 674 (1984).
- T.G. Waddell, W. Stöcklin, T.A. Geissman, Tetrahedron Letters, 1313 (1969);
- W. Stöcklin, T.G. Waddell, T.A. Geissman, Tetrahedron,26, 2397 (1970).
- Gu Yuan-xing, Acta Physica, 31, 963 (1982).
- Goldberg, I. Deja, M. Rey, A. S. Dreiding, Helv. Chim. Acta, 63, 2455 (1980).
- Xu Xing-xiang, Zhu Jie, Zhou Wei-shan, Kexue Tongbao, 27, 1022 (1982). ibid., 28, 859 (1982).
- Xu Xing-xiang, Huang Da-zhong, Zhu Jie and Zhou Wei-shan, Acta Chimica Sinica, 40, 1081 (1982).
- Zhou Wei-shan, Zhang Lian, Xu Xing-xiang, ibid., 43, 845 (1985);
Cited by
Sorted by citations
The Biosynthesis of Artemisinin (Qinghaosu) and the Phytochemistry of Artemisia annua L. (Qinghao)
Brown, G. D. (2010) · Molecules · doi:10.3390/molecules15117603 · Cited by 363 · see citing works
Semisynthetic Artemisinin, the Chemical Path to Industrial Production
Turconi, J., Griolet, F., Guevel, R., Oddon, G., Villa, R., Geatti, A., Hvala, M., Rossen, K., Göller, R., & Burgard, A. (2014) · Organic Process Research & Development · doi:10.1021/op4003196 · Cited by 228 · see citing works
In vivo transformations of dihydroartemisinic acid in Artemisia annua plants
Brown, G. D., & Sy, L.-K. (2004) · Tetrahedron · doi:10.1016/j.tet.2003.11.070 · Cited by 183 · see citing works
The mechanism of the spontaneous autoxidation of dihydroartemisinic acid
Sy, L.-K., & Brown, G. D. (2002) · Tetrahedron · doi:10.1016/s0040-4020(01)01193-0 · Cited by 129 · see citing works
The Total synthesis of (+)-artemisinin and (+)-9-desmethyltemesinin
Avery, M. A., Jennings-White, C., & Chong, W. K. M. (1987) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)96582-1 · Cited by 114 · see citing works
Stereoselective synthesis of artemisinin
Ravindranathan, T., Anil Kumar, M., Menon, R. B., & Hiremath, S. V. (1990) · Tetrahedron Letters · doi:10.1016/s0040-4039(00)94621-5 · Cited by 103 · see citing works
In vivo transformations of artemisinic acid in Artemisia annua plants
Brown, G. D., & Sy, L.-K. (2007) · Tetrahedron · doi:10.1016/j.tet.2007.06.062 · Cited by 100 · see citing works
A total synthesis of the antimarial natural product (+)-qinghaosu
Hsing-Jang, L., Wen-Lung, Y., & Sew, Y. C. (1993) · Tetrahedron Letters · doi:10.1016/0040-4039(93)88052-k · Cited by 78 · see citing works
Synthesis of 6,7-dehydroartemisinic acid
Sy, L.-K., & Brown, G. D. (2001) · Journal of the Chemical Society, Perkin Transactions 1 · doi:10.1039/b104471k · Cited by 19 · see citing works
- Authors
- Zhou, W.-S.
- Affiliations
- Shanghai Institute of Organic Chemistry (CN)
- Corresponding author
- Zhou, W.-S.
- Venue
- Pure and Applied Chemistry
- Publisher
- Walter de Gruyter GmbH
- Published
- 1986-01-01
- Volume
- 58
- Issue
- 5
- Pages
- 817-824
- ISSN
- 0033-4545 (ISSN-L)
- 1365-3075
- OpenAlex
- W2030617777
- Cited by
- 47
- References
- 1
- Citations by year
- 2022: 1 · 2018: 1 · 2017: 1 · 2014: 3
- FWCI
- 0.86
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Pure and Applied Chemistry (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biological Activity of Diterpenoids and Biflavonoids
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Keywords
- total synthesis, sesquiterpene lactones, artemisinin derivatives, natural product synthesis
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