Stereoselective total synthesis of (+)-artemisinin, the antimalarial constituent of Artemisia annua L
Abstract
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTStereoselective total synthesis of (+)-artemisinin, the antimalarial constituent of Artemisia annua LMitchell A. Avery, Wesley K. M. Chong, and Clive Jennings-WhiteCite this: J. Am. Chem. Soc. 1992, 114, 3, 974–979Publication Date (Print):January 1, 1992Publication History Published online1 May 2002Published inissue 1 January 1992https://pubs.acs.org/doi/10.1021/ja00029a028https://doi.org/10.1021/ja00029a028research-articleACS PublicationsRequest reuse permissionsArticle Views5559Altmetric-Citations213LEARN 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
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
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 [231]
Cited by
Sorted by citations
Engineering a mevalonate pathway in Escherichia coli for production of terpenoids
Martin, V. J. J., Pitera, D. J., Withers, S. T., Newman, J. D., & Keasling, J. D. (2003) · Nature Biotechnology · doi:10.1038/nbt833 · Cited by 1,720 · see citing works
“Furthermore, because of the complexity of these molecules, the chemical syntheses of terpenoids are inherently difficult and expensive and produce relatively low yield”
BackgroundIdentification of an antimalarial synthetic trioxolane drug development candidate
Vennerstrom, J. L., Arbe‐Barnes, S., Brun, R., Charman, S. A., Chiu, F. C. K., Chollet, J., Dong, Y., Dorn, A., Hunziker, D., Matile, H., et al. (2004) · Nature · doi:10.1038/nature02779 · Cited by 622 · see citing works
“However, as a drug class, the artemisinins suffer from chemica”
BackgroundThe 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
Shiba, Y., Paradise, E. M., Kirby, J., Ro, D., & Keasling, J. D. (2006) · Metabolic Engineering · doi:10.1016/j.ymben.2006.10.005 · Cited by 354 · see citing works
Artemisinin and the antimalarial endoperoxides: from herbal remedy to targeted chemotherapy
Meshnick, S. R., Taylor, T. E., & Kamchonwongpaisan, S. (1996) · Microbiological Reviews · doi:10.1128/mmbr.60.2.301-315.1996 · Cited by 710 · see citing works
Ozonolysis Applications in Drug Synthesis
Ornum, S. G. V., Champeau, R. M., & Pariza, R. J. (2006) · Chemical Reviews · doi:10.1021/cr040682z · Cited by 284 · see citing works
Synthetic peroxides as antimalarials
Tang, Y., Dong, Y., & Vennerstrom, J. L. (2004) · Medicinal Research Reviews · doi:10.1002/med.10066 · Cited by 277 · see citing works
Duke, M. V., Paul, R. N., Elsohly, H. N., Sturtz, G., & Duke, S. O. (1994) · International Journal of Plant Sciences · doi:10.1086/297173 · Cited by 252 · see citing works
Artemisinin, a Novel Antimalarial Drug: Biochemical and Molecular Approaches for Enhanced Production
Abdin, M. Z., Israr, M., Rehman, R. U., & Jain, S. K. (2003) · Planta Medica · doi:10.1055/s-2003-38871 · Cited by 252 · see citing works
Green and Efficient: Iron-Catalyzed Selective Oxidation of Olefins to Carbonyls with O 2
González-de-Castro, Á., & Xiao, J. (2015) · Journal of the American Chemical Society · doi:10.1021/jacs.5b03956 · Cited by 249 · see citing works
Current status of artemisinin and its derivatives as antimalarial drugs
Dhingra, V., Rao, K. V., & Narasu, M. L. (1999) · Life Sciences · doi:10.1016/s0024-3205(99)00356-2 · Cited by 241 · see citing works
Antimalarial Activity of Artemisinin (Qinghaosu) and Related Trioxanes: Mechanism (s) of Action
Cumming, J. N., Ploypradith, P., & Posner, G. H. (1996) · Advances in pharmacology · doi:10.1016/s1054-3589(08)60952-7 · Cited by 241 · 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
Probing the Biology of Natural Products: Molecular Editing by Diverted Total Synthesis
Szpilman, A. M., & Carreira, E. M. (2010) · Angewandte Chemie International Edition · doi:10.1002/anie.200904761 · Cited by 221 · see citing works
Kapoor, R., Chaudhary, V., & Bhatnagar, A. K. (2007) · Mycorrhiza · doi:10.1007/s00572-007-0135-4 · Cited by 211 · see citing works
“Photosynthetic pigments were extracted in dimethyl sulfoxide, and absorbance of the decant was taken at 480, 510, 645, and 663 nm. Chlorophyll-a, chlorophyll-b and carotenoid concentrations (mg/g, fresh weight) were calculated using the equations given by Arnon (1949) .”
MethodZhang, L., Jing, F., Li, F., Li, M., Wang, Y., Wang, G., Sun, X., & Tang, K. (2009) · Biotechnology and Applied Biochemistry · doi:10.1042/ba20080068 · Cited by 206 · see citing works
Sulfones and sulfoxides in the total synthesis of biologically active natural compounds
Prilezhaeva, E. N. (2000) · Russian Chemical Reviews · doi:10.1070/rc2000v069n05abeh000561 · Cited by 188 · see citing works
Yield enhancement strategies for artemisinin production by suspension cultures of Artemisia annua
Baldi, A., & Dixit, V. K. (2007) · Bioresource Technology · doi:10.1016/j.biortech.2007.06.061 · Cited by 176 · see citing works
“Synthesis of artemisinin has not proved to be commercially feasible (Avery et al., 1992) and low yield from natural source (E1Sohly et al.”
BackgroundNatural product synthesis in the age of scalability
Kuttruff, C. A., Eastgate, M. D., & Baran, P. S. (2013) · Natural Product Reports · doi:10.1039/c3np70090a · Cited by 171 · see citing works
Artemisinin, a miracle of traditional Chinese medicine
Kong, L. Y., & Tan, R. X. (2015) · Natural Product Reports · doi:10.1039/c5np00133a · Cited by 169 · see citing works
Fisher, T. J., & Dussault, P. H. (2017) · Tetrahedron · doi:10.1016/j.tet.2017.03.039 · Cited by 159 · see citing works
Artemisinin: current state and perspectives for biotechnological production of an antimalarial drug
Liu, C., Zhao, Y., & Wang, Y. (2006) · Applied Microbiology and Biotechnology · doi:10.1007/s00253-006-0452-0 · Cited by 158 · see citing works
“The total organic synthesis is very complicated with low yields, and economically unattractive (Avery et al. 1992; Xu et al. 1986).”
Beyond malaria: The inhibition of viruses by artemisinin-type compounds
Efferth, T. (2018) · Biotechnology Advances · doi:10.1016/j.biotechadv.2018.01.001 · Cited by 157 · see citing works
“Although total synthesis is possible (Schmid and Hofheinz, 1983; Ravindranathan et al., 1990; Avery et al., 1992), it is not routinely done, because it is too time-consuming and not economical.”
BackgroundTotal Synthesis of the Antimalarial Sesquiterpene Peroxide Qinghaosu and Yingzhaosu A
Zhou, W.-S., & Xu, X.-X. (1994) · Accounts of Chemical Research · doi:10.1021/ar00043a005 · Cited by 147 · see citing works
A Concise Synthesis of (+)-Artemisinin
Zhu, C., & Cook, S. P. (2012) · Journal of the American Chemical Society · doi:10.1021/ja3061479 · Cited by 152 · see citing works
Ferreira, J. F. S., Laughlin, J. C., Delabays, N., & de Magalhães, P. M. (2005) · Plant Genetic Resources · doi:10.1079/pgr200585 · Cited by 130 · see citing works
“Complete chemical (de novo) synthesis of artemisinin was achieved by several research groups (Schmid and Hofheinz, 1983; Xu et al., 1986; Ravindranathan et al., 1990; Avery et al., 1992).”
BackgroundThe 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
Floral Morphology of Artemisia annua with Special Reference to Trichomes
Janick, J. (1995) · International Journal of Plant Sciences · doi:10.1086/297304 · Cited by 129 · see citing works
Crespo, M. D. P., Avery, T. D., Hanssen, E. G., Fox, E., Robinson, T. V., Valente, P., Taylor, D. K., & Tilley, L. M. (2007) · Antimicrobial Agents and Chemotherapy · doi:10.1128/aac.00609-07 · Cited by 126 · see citing works
Production of the new antimalarial drug artemisinin in shoot cultures of Artemisia annua L.
Woerdenbag, H. J., Lüers, J. F. J., van Uden, W., Pras, N., Malingré, T. M., & Alfermann, A. W. (1993) · Plant Cell Tissue and Organ Culture (PCTOC) · doi:10.1007/bf00029850 · Cited by 120 · see citing works
Rai, R., Meena, R. P., Smita, S. S., Shukla, A., Kumar, S., & Rai, S. P. (2011) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2011.09.004 · Cited by 116 · see citing works
Artemisinin production by transformed roots of Artemisia annua
Weathers, P. J., Cheetham, R. D., Follansbee, E., & Teoh, K. H. (1994) · Biotechnology Letters · doi:10.1007/bf00149632 · Cited by 117 · see citing works
“The unique endoperoxide bridge found in the active forms of AN and its derivatives make organic synthesis economically impracticT1 for large scale production ( Avery et al., 1992).”
BackgroundAntimalarial peroxides: advances in drug discovery and design
Slack, R. D., Jacobine, A. M., & Posner, G. H. (2011) · MedChemComm · doi:10.1039/c2md00277a · Cited by 113 · see citing works
Metabolic flux elucidation for large-scale models using 13C labeled isotopes
Suthers, P. F., Burgard, A. P., Dasika, M. S., Nowroozi, F. F., Dien, S. V., Keasling, J. D., & Maranas, C. D. (2007) · Metabolic Engineering · doi:10.1016/j.ymben.2007.05.005 · Cited by 101 · see citing works
Transgenic approach to increase artemisinin content in Artemisia annua L.
Tang, K., Shen, Q., Yan, T., & Fu, X. (2014) · Plant Cell Reports · doi:10.1007/s00299-014-1566-y · Cited by 96 · see citing works
“Organic total synthesis was difficult and costly (Avery et al. 1992; Constantino et al. 1996), and was considered difficult for commercial production.”
BackgroundNiwa, Y., & Shimizu, M. (2003) · Journal of the American Chemical Society · doi:10.1021/ja029639o · Cited by 99 · see citing works
Fattorusso, E., & Taglialatela‐Scafati, O. (2009) · Marine Drugs · doi:10.3390/md7020130 · Cited by 95 · see citing works
“Totally synthetic routes to artemisinin have been developed [57], but their complexity suggests that they will very unlikely supplant the natural extract as a drug supply.”
BackgroundEnhancement of artemisinin content and biomass in Artemisia annua by exogenous GA3 treatment
Banyai, W., Mii, M., & Supaibulwatana, K. (2010) · Plant Growth Regulation · doi:10.1007/s10725-010-9510-9 · Cited by 89 · see citing works
State of the art of the production of the antimalarial compound artemisinin in plants
Geldre, E. V., Vergauwe, A., & den Eeckhout, E. V. (1997) · Plant Molecular Biology · doi:10.1023/a:1005716600612 · Cited by 84 · see citing works
RECENT ADVANCES IN THE SYNTHESIS OF SULFOXIDES FROM SULFIDES
Mata, E. G. (1996) · Phosphorus, sulfur, and silicon and the related elements · doi:10.1080/10426509608038790 · Cited by 83 · see citing works
The Claisen rearrangement in the syntheses of bioactive natural products
Majumdar, K. C., & Nandi, R. K. (2013) · Tetrahedron · doi:10.1016/j.tet.2013.06.003 · Cited by 82 · see citing works
Avery, M. A., Alvim‐Gaston, M., Vroman, J. A., Wu, B., Ager, A. L., Peters, W., Robinson, B. L., & Charman, W. N. (2002) · Journal of Medicinal Chemistry · doi:10.1021/jm020142z · Cited by 80 · see citing works
Self-citationA 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
Lin, X., Zhou, Y., Zhang, J., Lu, X., Zhang, F., Shen, Q., Wu, S., Chen, Y., Wang, T., & Tang, K. (2011) · Biotechnology and Applied Biochemistry · doi:10.1002/bab.13 · Cited by 80 · see citing works
Progress in the research of artemisinin-related antimalarials: An update
Woerdenbag, H. J., Pras, N., van Uden, W., Wallaart, T. E., Beekman, A. C., & Lugt, C. (1994) · Pharmacy World & Science · doi:10.1007/bf01872865 · Cited by 77 · see citing works
Sharma, R. P., & Bhattacharya, A. K. (1999) · Heterocycles · doi:10.3987/rev-98-505 · Cited by 77 · see citing works
Synthetic medicinal chemistry of selected antimalarial natural products
Kumar, V., Mahajan, A., & Chibale, K. (2008) · Bioorganic & Medicinal Chemistry · doi:10.1016/j.bmc.2008.10.072 · Cited by 76 · see citing works
A concise stereoselective total synthesis of (+)-artemisinin
Yadav, J. S., Thirupathaiah, B., & Pabbaraja, S. (2010) · Tetrahedron · doi:10.1016/j.tet.2010.01.051 · Cited by 73 · see citing works
Avery, M. A., Mehrotra, S., Johnson, T. L., Bonk, J. D., Vroman, J. A., & Miller, R. E. (1996) · Journal of Medicinal Chemistry · doi:10.1021/jm9603577 · Cited by 72 · see citing works
Self-citationStereoselective total synthesis of (+)-artemisinin
Yadav, J. S., Babu, R. S., & Sabitha, G. (2003) · Tetrahedron Letters · doi:10.1016/s0040-4039(02)02500-5 · Cited by 70 · see citing works
An Efficient Chemoenzymatic Synthesis of Dihydroartemisinic Aldehyde
Demiray, M., Tang, X., Wirth, T., Faraldos, J. A., & Allemann, R. K. (2017) · Angewandte Chemie International Edition · doi:10.1002/anie.201609557 · Cited by 68 · see citing works
Singh, N. D., Kumar, S., & Daniell, H. (2016) · Plant Biotechnology Journal · doi:10.1111/pbi.12476 · Cited by 67 · see citing works
“Although organic synthesis of artemisinin is possible, its low yield makes it economically nonviable as a mean of drug production (Avery et al. 1992).”
BackgroundKumar, R., Mohanakrishnan, D., Sharma, A., Kaushik, N. K., Kalia, K., Sinha, A. K., & Sahal, D. (2010) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2010.08.049 · Cited by 64 · see citing works
Szpilman, A. M., & Carreira, E. M. (2010) · Angewandte Chemie · doi:10.1002/ange.200904761 · Cited by 63 · see citing works
Oguri, H., Hiruma, T., Yamagishi, Y., Oikawa, H., Ishiyama, A., Otoguro, K., Yamada, H., & Ōmura, S. (2011) · Journal of the American Chemical Society · doi:10.1021/ja200374q · Cited by 58 · see citing works
Tiwari, M. K., & Chaudhary, S. (2020) · Medicinal research reviews (Print) · doi:10.1002/med.21657 · Cited by 47 · see citing works
Avery, M. A., Mehrotra, S., Bonk, J. D., Vroman, J. A., Goins, D. K., & Miller, R. E. (1996) · Journal of Medicinal Chemistry · doi:10.1021/jm960200e · Cited by 58 · see citing works
Self-citationA Novel Asymmetric Total Synthesis of (+)-Artemisinin
Constantino, M. G., Beltrame, M., da Silva, G. V. J., & Zukerman-Schpector, J. (1996) · Synthetic Communications · doi:10.1080/00397919608003621 · Cited by 58 · see citing works
Patel, O. P., Beteck, R. M., & Legoabe, L. J. (2021) · European Journal of Medicinal Chemistry · doi:10.1016/j.ejmech.2021.113193 · Cited by 56 · see citing works
Strategies for Coupling Molecular Units if Subsequent Decoupling Is Required
Bielski, R., & Witczak, Z. J. (2012) · Chemical Reviews · doi:10.1021/cr200338q · Cited by 56 · see citing works
Jiang, Z. W., Zhao, T., Zhen, S. J., Li, C. M., Li, Y. F., & Huang, C. Z. (2021) · Journal of Materials Chemistry A · doi:10.1039/d1ta01278a · Cited by 52 · see citing works
Synthesis of (+)-artemisinin and (+)-deoxoartemisinin from arteannuin B and arteannuic acid
Nowak, D. M., & Lansbury, P. T. (1998) · Tetrahedron · doi:10.1016/s0040-4020(97)10286-1 · Cited by 51 · see citing works
Synthetic chemistry fuels interdisciplinary approaches to the production of artemisinin
Corsello, M. A., & Garg, N. K. (2014) · Natural Product Reports · doi:10.1039/c4np00113c · Cited by 53 · see citing works
Ozone, chemical reactivity and biological functions
Audran, G., Marque, S. R. A., & Santelli, M. (2018) · Tetrahedron · doi:10.1016/j.tet.2018.09.023 · Cited by 50 · see citing works
류지현, Lee, S.-J., 김미주, et al. (2011) · Journal of the Korean Society of Food Science and Nutrition · doi:10.3746/jkfn.2011.40.4.509 · Cited by 50 · see citing works
In vitro Evaluation of Hydroxyl and Nitric Oxide Radical Scavenging Activities of Artemether
Olabinr, B. M., Odedire, O. O., Olaleye, M. T., et al. (2010) · Research Journal of Biological Sciences · doi:10.3923/rjbsci.2010.102.105 · Cited by 50 · see citing works
Liu, C., Chen, G., Wang, Y., & Ouyang, F. (2003) · Process Biochemistry · doi:10.1016/s0032-9592(02)00294-7 · Cited by 49 · see citing works
Artemisiaannua: Botany, Horticulture, Pharmacology
Ferreira, J., Simon, J. E., & Janick, J. (1996) · Horticultural reviews · doi:10.1002/9780470650622.ch6 · Cited by 50 · see citing works
Synthetic Strategies for Peroxide Ring Construction in Artemisinin
Андреевна, В. В., Yaremenko, I. A., Ilovaisky, A. I., & Terent'ev, A. O. (2017) · Molecules · doi:10.3390/molecules22010117 · Cited by 49 · see citing works
“Other Methods Avery and colleagues developed quite a different precursor for the construction of bicyclic peroxide artem sinin fragment—vinyl s lane 51 (Scheme 9) [49,50].”
BackgroundKrieger, J., Smeilus, T., Kaiser, M., Seo, E., Efferth, T., & Giannis, A. (2018) · Angewandte Chemie International Edition · doi:10.1002/anie.201802015 · Cited by 48 · see citing works
O’Neill, P. M. (2005) · Expert Opinion on Investigational Drugs · doi:10.1517/13543784.14.9.1117 · Cited by 47 · see citing works
Chen, Y., Evarts, J., Torres, E., et al. (2002) · Organic Letters · doi:10.1021/ol026377m · Cited by 47 · see citing works
Metabolic engineering of chloroplasts for artemisinic acid biosynthesis and impact on plant growth
Saxena, B., Subramani, M., Malhotra, K., Bhavesh, N. S., Potlakayala, S. D., & Kumar, S. B. (2014) · Journal of Biosciences · doi:10.1007/s12038-013-9402-z · Cited by 46 · see citing works
Naeem, M., Sadiq, Y., Jahan, A., Nabi, A., Aftab, T., & Khan, M. M. A. (2020) · Ecotoxicology and Environmental Safety · doi:10.1016/j.ecoenv.2020.110851 · Cited by 46 · see citing works
Novel organic peroxygen reagents for use in organic synthesis
Heaney, H. (1993) · Topics in current chemistry · doi:10.1007/3-540-56252-4_22 · Cited by 46 · see citing works
Maerki, S. (2006) · Journal of Antimicrobial Chemotherapy · doi:10.1093/jac/dkl209 · Cited by 45 · see citing works
(2007) · AFRICAN JOURNAL OF BIOTECHNOLOGY · doi:10.5897/ajb2007.000-2198 · Cited by 43 · see citing works
A Hydrogen Peroxide Based Access to Qinghaosu (Artemisinin)
Hao, H., Li, Y., Han, W., & Wu, Y. (2011) · Organic Letters · doi:10.1021/ol2015434 · Cited by 44 · see citing works
KOVAL', I. V. (2007) · Russian Journal of Organic Chemistry · doi:10.1134/s1070428007030013 · Cited by 44 · see citing works
Factors influencing artemisinin production from shoot cultures of Artemisia annua L.
Liu, C., Guo, C., Wang, Y., & Ouyang, F. (2003) · World Journal of Microbiology and Biotechnology · doi:10.1023/a:1025158416832 · Cited by 43 · see citing works
“The total organic synthesis has been established, but is very complicated, with low yields, and therefore economically unattractive (Xu et al. 1986; Ravindranathan et al. 1990; Avery et al. 1992 ).”
BackgroundSynthesis and reactions of 11-azaartemisinin and derivatives
Torok, D. S., & Ziffer, H. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(94)02419-c · Cited by 43 · see citing works
Coimbra, P., Blanco, M. R., Silva, H. S. R. C., et al. (2006) · Journal of Chemical & Engineering Data · doi:10.1021/je060015y · Cited by 43 · see citing works
Jha, P., Ram, M., Khan, M. A., Kiran, U., Mahmooduzzafar, M., & Abdin, M. Z. (2011) · Industrial Crops and Products · doi:10.1016/j.indcrop.2010.12.011 · Cited by 44 · see citing works
Potent Antimalarial 1,2,4‐Trioxanes through Perhydrolysis of Epoxides
Hao, H., Wittlin, S., & Wu, Y. (2013) · Chemistry - A European Journal · doi:10.1002/chem.201300076 · Cited by 42 · see citing works
Liu, C., Wang, Y., Guo, C., Ouyang, F., Ye, H., & Li, G. (1998) · Plant Science · doi:10.1016/s0168-9452(98)00086-7 · Cited by 42 · see citing works
Cadinanes from Artemisia annua that may be intermediates in the biosynthesis of artemisinin
Brown, G. D. (1994) · Phytochemistry · doi:10.1016/s0031-9422(00)89788-5 · Cited by 41 · see citing works
Naeem, M., Nabi, A., Aftab, T., & Khan, M. M. A. (2019) · PROTOPLASMA · doi:10.1007/s00709-019-01475-y · Cited by 40 · see citing works
Chen, Y., Shen, Q., Wang, Y., Wang, T., Wu, S., Zhang, L., Lu, X., Zhang, F., Jiang, W., Qiu, B., et al. (2013) · Plant Biotechnology Reports · doi:10.1007/s11816-012-0262-z · Cited by 38 · see citing works
Kim, E. J., Kim, G. T., Kim, B. M., Lim, E. G., Kim, S.-Y., & Kim, Y. M. (2017) · BMC Complementary and Alternative Medicine · doi:10.1186/s12906-017-1702-7 · Cited by 39 · see citing works
“In previous studies, they determined that when using Artemisia annua Linné on extracts from breast cancer, cervical carcinoma cells, stomach cancer, and for cell growth inhibitory effect that there is a cancer cell [10, 11].”
BackgroundIn vitro activity of anti-malarial ozonides against an artemisinin-resistant isolate
Baumgärtner, F., Jourdan, J., Scheurer, C., Blasco, B., Campo, B., Mäser, P., & Wittlin, S. (2017) · Malaria Journal · doi:10.1186/s12936-017-1696-0 · Cited by 37 · see citing works
“Since the starting material artemisinin is a natural product, its production is limited to the availability of the plant [4, 7], although several total syntheses of artemisinin have been described [8].”
BackgroundUse of Gamma Radiation Techniques in Peaceful Applications
Almayah, B. A. (2019) · IntechOpen eBooks · doi:10.5772/intechopen.78481 · Cited by 38 · see citing works
Synthesis and structure-activity relationships of peroxidic antimalarials based on artemisinin
Avery, M. A., Alvim‐Gaston, M., & Woolfrey, J. R. (1999) · Advances in medicinal chemistry · doi:10.1016/s1067-5698(99)80005-4 · Cited by 36 · see citing works
Self-citationAdvances in the Chemical Synthesis of Artemisinin
Wang, Z., Yang, L., Yang, X., & Zhang, X. (2014) · Synthetic Communications · doi:10.1080/00397911.2014.884225 · Cited by 35 · see citing works
Gupta, S. K., Sahoo, S. K., & Choudhury, J. (2016) · Organometallics · doi:10.1021/acs.organomet.6b00337 · Cited by 35 · see citing works
Aftab, T., Khan, M. M. A., Naeem, M., Idrees, M., Siddiqi, T. O., Moinuddin, M., & Varshney, L. (2014) · Carbohydrate Polymers · doi:10.1016/j.carbpol.2014.04.045 · Cited by 35 · see citing works
Chemistry of artemisinin: an overview
Webster, H. K., & Lehnert, E. K. (1994) · Transactions of the Royal Society of Tropical Medicine and Hygiene · doi:10.1016/0035-9203(94)90467-7 · Cited by 35 · see citing works
Posner, G. H., Oh, C. H., Gerena, L., & Milhous, W. K. (1995) · Heteroatom Chemistry · doi:10.1002/hc.520060205 · Cited by 35 · see citing works
Synthesis of Indolin‐3‐ones and Tetrahydro‐4‐quinolones from α‐Imino Esters
Shimizu, M., Takao, Y., Katsurayama, H., et al. (2013) · Asian Journal of Organic Chemistry · doi:10.1002/ajoc.201200174 · Cited by 34 · see citing works
Wang, H., Jia, R., Hong, M., et al. (2021) · Green Chemistry · doi:10.1039/d1gc01931g · Cited by 34 · see citing works
Enhanced artemisinin production by cell cultures of Artemisia annua
Baldi, A., & Dixit, V. K. (2008) · Current Trends in Biotechnology and Pharmacy · Cited by 34 · see citing works
- Authors
- Avery, M. A., Chong, W. K. M., & Jennings-White, C.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 1992-01
- Volume
- 114
- Issue
- 3
- Pages
- 974-979
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2079682999
- Cited by
- 250
- References
- 0
- Citations by year
- 2026: 1 · 2025: 6 · 2024: 6 · 2023: 3 · 2022: 4 · 2021: 8 · 2020: 7 · 2019: 7 · 2018: 10 · 2017: 13 · 2016: 8 · 2015: 7 · 2014: 11 · 2013: 10 · 2012: 10
- FWCI
- 4.62
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Cancer Research › Sesquiterpenes and Asteraceae Studies
- Physical Sciences › Chemistry › Organic Chemistry › Organic Chemistry Synthesis Methods
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Biological Activity of Diterpenoids and Biflavonoids
- Keywords
- artemisinin, total synthesis, stereoselective synthesis, Artemisia annua, antimalarial compounds, sesquiterpene lactones, endoperoxides
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
