Catalysed oxygenation of allylic hydroperoxides derived from qinghao (artemisinic) acid. Conversion of qinghao acid into dehydroginghaosu (artemisitene) and qinghaosu (artemisinin)

Qinghaosu (Artemisinin): an Antimalarial Drug from China

Klayman, D. L. (1985) · Science · doi:10.1126/science.3887571 · Cited by 2,186 · see citing works

Total synthesis of arteannuin and deoxyarteannuin

Xing-Xiang, X., Jie, Z., Da-Zhong, H., & Wei-Shan, Z. (1986) · Tetrahedron · doi:10.1016/s0040-4020(01)87487-1 · Cited by 181 · see citing works

Practical conversion of artemisinic acid in desoxyartemisinin

Jung, M., ElSohly, H. N., Croom, E. M., McPhail, A. T., & McPhail, D. R. (1986) · The Journal of Organic Chemistry · doi:10.1021/jo00376a070 · Cited by 58 · see citing works

A short and stereospecific synthesis of (+)-deoxoartemisinin and (−)-deoxodesoxyartemisinin

Jung, M., Li, X., Bustos, D. A., ElSohly, H. N., & McChesney, J. D. (1989) · Tetrahedron Letters · doi:10.1016/s0040-4039(01)93831-6 · Cited by 56 · see citing works

High-level semi-synthetic production of the potent antimalarial artemisinin

Paddon, C. J., Westfall, P. J., Pitera, D. J., Benjamin, K., Fisher, K., McPhee, D., Leavell, M. D., Tai, A., Main, A., Eng, D., et al. (2013) · Nature · doi:10.1038/nature12051 · Cited by 2,060 · see citing works

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

Understanding Reactivity Patterns of Radical Cations

Schmittel, M., & Burghart, A. (1997) · Angewandte Chemie International Edition in English · doi:10.1002/anie.199725501 · Cited by 362 · see citing works

A Continuous‐Flow Process for the Synthesis of Artemisinin

Kopetzki, D., Lévesque, F., & Seeberger, P. H. (2013) · Chemistry - A European Journal · doi:10.1002/chem.201204558 · Cited by 218 · 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

Antimalarial sesquiterpenes from tubers of Cyperus rotundus: structure of 10,12-Peroxycalamenene, a sesquiterpene endoperoxide

Thebtaranonth, C., Thebtaranonth, Y., Wanauppathamkul, S., & Yuthavong, Y. (1995) · Phytochemistry · doi:10.1016/0031-9422(95)00260-e · Cited by 177 · 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

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

An antimalarial peroxide from Amomum krervanh Pierre

Kamchonwongpaisan, S., Nilanonta, C., Tarnchompoo, B., Thebtaranonth, C., Thebtaranonth, Y., Yuthavong, Y., Kongsaeree, P., & Clardy, J. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)00152-3 · Cited by 69 · see citing works

A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides

Sy, L., Brown, G. D., & Haynes, R. K. (1998) · Tetrahedron · doi:10.1016/s0040-4020(98)00148-3 · Cited by 66 · see citing works

Artemisinin‐derived antimalarial endoperoxides from bench‐side to bed‐side: Chronological advancements and future challenges

Tiwari, M. K., & Chaudhary, S. (2020) · Medicinal research reviews (Print) · doi:10.1002/med.21657 · Cited by 47 · see citing works

Zum Verständnis der Reaktionsmuster von Radikalkationen

Schmittel, M., & Burghart, A. (1997) · Angewandte Chemie · doi:10.1002/ange.19971092304 · Cited by 59 · see citing works

Mechanisms for the Formation of Isoprostane Endoperoxides from Arachidonic Acid

Yin, H., Havrilla, C. M., Gao, L., Morrow, J. D., & Porter, N. A. (2003) · Journal of Biological Chemistry · doi:10.1074/jbc.m300604200 · Cited by 58 · see citing works

Concise synthesis of yingzhaosu C and epi-yingzhaosu C by peroxyl radical cyclization. Assignment of relative configuration

Boukouvalas, J., Pouliot, R., & Fréchette, Y. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)00714-n · Cited by 55 · 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

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 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

Continuous Flow Reduction of Artemisinic Acid Utilizing Multi‐Injection Strategies—Closing the Gap Towards a Fully Continuous Synthesis of Antimalarial Drugs

Pieber, B., Glasnov, T. N., & Kappe, C. O. (2015) · Chemistry - A European Journal · doi:10.1002/chem.201406439 · Cited by 46 · see citing works

Extraction of artemisinin and artemisinic acid: preparation of artemether and new analogues

Haynes, R. K., & Vonwiller, S. C. (1994) · Transactions of the Royal Society of Tropical Medicine and Hygiene · doi:10.1016/0035-9203(94)90466-9 · Cited by 45 · see citing works

Convenient Access Both to Highly Antimalaria‐Active 10‐Arylaminoartemisinins, and to 10‐Alkyl Ethers Including Artemether, Arteether, and Artelinate

Haynes, R. K., Chan, H., Ho, W., Ko, C. K., Gerena, L., Kyle, D. E., Peters, W., & Robinson, B. L. (2005) · ChemBioChem · doi:10.1002/cbic.200400366 · Cited by 38 · see citing works

Synthesis and antimalarial activities of structurally simplified 1,2,4‐trioxanes related to artemisinin

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

Peroxidic Antimalarials

Jefford, C. W. (1997) · Advances in Drug Research · doi:10.1016/s0065-2490(97)80016-0 · Cited by 33 · see citing works

Syntheses of dihydroartemisinic acid and dihydro-epi-deoxyarteannuin B incorporating a stable isotope label at the 15-position for studies into the biosynthesis of artemisinin

Sy, L.-K., Zhu, N.-Y., & Brown, G. D. (2001) · Tetrahedron · doi:10.1016/s0040-4020(01)00711-6 · Cited by 27 · see citing works

A facile and scalable synthesis of qinghaosu (artemisinin)

Chen, H.-J., Han, W., Hao, H., & Wu, Y. (2012) · Tetrahedron · doi:10.1016/j.tet.2012.11.056 · Cited by 26 · see citing works

Six-Membered Ring Systems: With O and/or S Atoms

Hepworth, J. D., & Heron, B. M. (1989) · ChemInform · doi:10.1002/chin.200305241 · Cited by 26 · see citing works

Reactions of Artemisinin and Arteether with Acid: Implications for Stability and Mode of Antimalarial Action

Drew, M. G. B., Metcalfe, J. Z., Dascombe, M. J., & Ismail, F. M. D. (2006) · Journal of Medicinal Chemistry · doi:10.1021/jm060673d · Cited by 23 · see citing works

Artemisinin: An Endoperoxidic Antimalarial from Artemisia annua L.

Ziffer, H., Highet, R. J., & Klayman, D. L. (1997) · Springer eBooks · doi:10.1007/978-3-7091-6527-0_2 · Cited by 23 · see citing works

A golden phoenix arising from the herbal nest — A review and reflection on the study of antimalarial drug Qinghaosu

Li, Y., & Wu, Y. (2010) · Frontiers of Chemistry in China · doi:10.1007/s11458-010-0214-5 · Cited by 20 · see citing works

Biomimetic synthesis of arteannuin h and the 3,2-rearrangement of allylic hydroperoxides

Sy, L., Ngo, K., & Brown, G. D. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00987-4 · Cited by 19 · see citing works

The preparation of D-ring-contracted analogues of Qinghaosu (Artemisinin) from Qinghao (Artemisinic) acid and their In vitro activity against Plasmodium falciparum

Haynes, R. K., Vonwiller, S. C., & Wang, H. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)00806-n · Cited by 19 · see citing works

Autoxidation of 4-amorphen-11-ol and the biogenesis of nor- and seco-amorphane sesquiterpenes from fabiana imbricata

Ngo, K., & Brown, G. D. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00986-2 · Cited by 17 · see citing works

Nonclassical CH−π Supramolecular Interactions in Artemisinic Acid Favor a Single Conformation, Yielding High Diastereoselectivity in the Reduction with Diazene

CASTRO, B., Chaudret, R., Ricci, G., Kurz, M. E., Ochsenbein, P., Kretzschmar, G., Kraft, V., Rossen, K., & Eisenstein, O. (2014) · The Journal of Organic Chemistry · doi:10.1021/jo500233z · Cited by 15 · see citing works

Rapid and Systematic Exploration of Chemical Space Relevant to Artemisinins: Anti-malarial Activities of Skeletally Diversified Tetracyclic Peroxides and 6-Aza-artemisinins

Bonepally, K. R., Takahashi, N., Matsuoka, N., Koi, H., Mizoguchi, H., Hiruma, T., Ochiai, K., Suzuki, S., Yamagishi, Y., Oikawa, H., et al. (2020) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.0c01017 · Cited by 15 · see citing works

Transition metals in organic synthesis: Hydroformylation, reduction, and oxidation

Markó, L., & Ungváry, F. (1992) · Journal of Organometallic Chemistry · doi:10.1016/0022-328x(92)83344-h · Cited by 13 · see citing works

Reactions of Hydroperoxides and Peroxides

Dussault, P. (1995) · Springer eBooks · doi:10.1007/978-94-007-0874-7_5 · Cited by 11 · see citing works

Joining Forces: Fermentation and Organic Synthesis for the Production of Complex Heterocycles

Gober, C. M., & Joullié, M. M. (2016) · The Journal of Organic Chemistry · doi:10.1021/acs.joc.6b01308 · Cited by 10 · see citing works

De novo identification and stability of the artemisinin pharmacophore: Studies of the reductive decomposition of deoxyartemisinins and deoxyarteethers and the implications for the mode of antimalarial action

Drew, M. G. B., Metcalfe, J. Z., Dascombe, M. J., & Ismail, F. M. D. (2007) · Journal of Molecular Structure THEOCHEM · doi:10.1016/j.theochem.2007.08.007 · Cited by 8 · see citing works

Seven-Membered Rings

KANE, J. M., & Peet, N. P. (1991) · Progress in heterocyclic chemistry · doi:10.1016/b978-0-08-040589-6.50021-7 · Cited by 8 · see citing works

Synthesis of Cyclic Peroxides

Korshin, E. E., & Bachi, M. D. (2009) · Patai's chemistry of functional groups · doi:10.1002/9780470682531.pat0351 · Cited by 8 · see citing works

Discovery of Antimalarial Drug Artemisinin and Beyond

Mao, W., Zhang, Y. X., & Zhang, A. (2012) · doi:10.1002/9781118219683.ch10 · Cited by 7 · see citing works

Carbon–carbon bond scission during the reactions of allylic hydroperoxides with some transition metal compounds. Results relevant to a recent proposal

Courtneidge, J. L. (1992) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39920000381 · Cited by 7 · see citing works

The formation of a peracetal and trioxane from an enol ether with Copper(II) triflate and oxygen: unexpected oxygenation of aldol intermediates

Vonwiller, S. C., Warner, J. A., Mann, S. T., & Haynes, R. K. (1997) · Tetrahedron Letters · doi:10.1016/s0040-4039(97)00349-3 · Cited by 5 · see citing works

Synthesis and Structural Diversification of Artemisinins towards the Generation of Potent Anti-malarial Agents

Oguri, H. (2021) · Chemistry Letters · doi:10.1246/cl.200920 · Cited by 6 · see citing works

Peroxyl Radicals in Synthesis

Boukouvalas, J., & Haynes, R. K. (2001) · doi:10.1002/9783527618293.ch48 · Cited by 6 · see citing works

Antimalarials

Smithson, D. C., Guiguemde, W. A., & Guy, R. K. (2010) · Burger's Medicinal Chemistry and Drug Discovery · doi:10.1002/0471266949.bmc234 · Cited by 5 · see citing works

An improved preparation of the desmethyl qinghao acid precursor of (±)-6,9-desmethylqinghaosu

Haynes, R. K., Lam, K., Wu, K., & Yeung, L. L. (1999) · Tetrahedron · doi:10.1016/s0040-4020(99)00543-8 · Cited by 3 · see citing works

Seven-Membered Rings

Kane, J. M., & Peet, N. P. (1990) · Progress in heterocyclic chemistry · doi:10.1016/b978-0-08-037070-5.50020-5 · Cited by 3 · see citing works

Identifying a kinetic model for the acid-catalyzed sequence of the artemisinin partial synthesis

Schulze, M., Triemer, S., Schenkendorf, R., Seidel‐Morgenstern, A., & Krewer, U. (2025) · Chemical Engineering Journal · doi:10.1016/j.cej.2025.167770 · Cited by 2 · see citing works

Artemisinin Chemical Research

(2018) · Elsevier eBooks · doi:10.1016/b978-0-12-813133-6.00003-2 · Cited by 2 · see citing works

How radical cations react? - Distonic radical cation mediated α(nucleophilic), β(radical)-dibenzoloxylation of donor ArCH = CHR

Zhao, Y. C., Li, W., Chen, Q.-Y., & Zhao, C.-X. (2001) · Research on Chemical Intermediates · doi:10.1163/156856701300356509 · Cited by 1 · see citing works

Preparation of chemically robust new artemisinin derivatives

(2003) · Expert Opinion on Therapeutic Patents · doi:10.1517/13543776.13.11.1763 · Cited by 1 · see citing works

Six-membered Rings with 1,2,4-Oxygen or Sulfur Atoms

Jefford, C. W. (1996) · Elsevier eBooks · doi:10.1016/b978-008096518-5.00136-2 · Cited by 1 · see citing works

Synthetic applications

Kagan, J. (1993) · Elsevier eBooks · doi:10.1016/b978-0-12-394320-0.50011-9 · Cited by 1 · see citing works

II. Monocyclic Sesquiterpenes

Goldsmith, D. J., Pirrung, M. C., & Morehead, A. T. (1997) · Total synthesis of natural products · doi:10.1002/9780470129739.ch2 · Cited by 1 · see citing works

Sesquiterpenoids (C15)

Talapatra, S. K., & Talapatra, B. (2014) · Springer eBooks · doi:10.1007/978-3-642-45410-3_7

Volume 6 References

(1996) · Elsevier eBooks · doi:10.1016/b978-008096518-5.00252-5

R. K. Haynes

(2011) · ChemMedChem · doi:10.1002/cmdc.201100313

Photochemical routes to artemisinin

Lancel, M., Tambosco, B., & Amara, Z. (2023) · Royal Society of Chemistry eBooks · doi:10.1039/bk9781837672301-00301

Catalyzed Oxygenation of Allylic Hydroperoxides Derived from Qinghao (Artemisinic) Acid. Conversion of Qinghao Acid into Dehydroqinghaosu (Artemisitene) and Qinghaosu (Artemisinin)

Haynes, R. K., & Vonwiller, S. C. (1990) · Rare & Special e-Zone (The Hong Kong University of Science and Technology)

Copper(II) Trifluoromethanesulfonate-Induced Cleavage Oxygenation of Allylic Hydroperoxides Derived from Qinghao Acid in the Synthesis of Qinghaosu Derivatives: Evidence for the Intermediacy of Enols

Vonwiller, S. C., Warner, J. A., Mann, S. T., & Haynes, R. K. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00150a009 · Cited by 48 · see citing works

The preparation of D-ring-contracted analogues of Qinghaosu (Artemisinin) from Qinghao (Artemisinic) acid and their In vitro activity against Plasmodium falciparum

Haynes, R. K., Vonwiller, S. C., & Wang, H. (1995) · Tetrahedron Letters · doi:10.1016/0040-4039(95)00806-n · Cited by 19 · see citing works

Efficient Preparation of Novel Qinghaosu (Artemisinin) Derivatives: Conversion of Qinghao (Artemisinic) Acid into Deoxoqinghaosu Derivatives and 5-Carba-4-deoxoartesunic Acid1

Haynes, R. K., & Vonwiller, S. C. (1992) · Synlett · doi:10.1055/s-1992-21384 · Cited by 36 · see citing works

A facile and scalable synthesis of qinghaosu (artemisinin)

Chen, H.-J., Han, W., Hao, H., & Wu, Y. (2012) · Tetrahedron · doi:10.1016/j.tet.2012.11.056 · Cited by 26 · see citing works