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Search for "artemisinin" in Full Text gives 39 result(s) in Beilstein Journal of Organic Chemistry.

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

  • Flavio Fanelli,
  • Giovanna Parisi,
  • Leonardo Degennaro and
  • Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

Graphical Abstract
  • is compatible with sensitive functional groups such as silyl ether, halogenes, and benzyl groups. A very nice application of this approach was the highly selective reduction of artemisinic acid to dihydroartemisinic acid, which are of interest in the synthesis of the antimalarial drug artemisinin
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Published 14 Mar 2017

A flow reactor setup for photochemistry of biphasic gas/liquid reactions

  • Josef Schachtner,
  • Patrick Bayer and
  • Axel Jacobi von Wangelin

Beilstein J. Org. Chem. 2016, 12, 1798–1811, doi:10.3762/bjoc.12.170

Graphical Abstract
  • photooxidations of citronellol [35][40][41][42], indanes [43], monoterpenes [36], furans [42], furfurals [44], thiols [37] and amines [45] as well as the syntheses of ascaridol [46] and artemisinin [47]. Related microreactor setups were applied to biphasic gas/liquid mixtures in the photochlorination of
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Published 11 Aug 2016

Rearrangements of organic peroxides and related processes

  • Ivan A. Yaremenko,
  • Vera A. Vil’,
  • Dmitry V. Demchuk and
  • Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Graphical Abstract
  • processes of important natural and synthetic peroxides are discussed separately. Keywords: artemisinin; Baeyer−Villiger; Criegee; Hock; peroxide; rearrangement; Introduction The chemistry of organic peroxides has more than a hundred-year history. Currently, organic peroxides are widely used as oxidizing
  • six-membered 1,2-dioxane [40][41][42], 1,2-dioxene [43], 1,2,4-trioxane [22][44][45] cycles. The naturally occuring peroxide artemisinin and its semisynthetic derivatives, artemether, arteether, and artesunate, are applied in large scale for malaria treatment [46][47]. Organic peroxides, their
  • photochemical route developed for the synthesis of artemisinin the Hock rearrangement of hydroperoxide 223 selectively affords enol 224. This reactive intermediate 224 is then finally oxidized into artemisinin (Scheme 66) [334]. 1.4 Kornblum−DeLaMare rearrangement The Kornblum−DeLaMare rearrangement (KDLM) is a
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Published 03 Aug 2016

Natural products in synthesis and biosynthesis II

  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 413–414, doi:10.3762/bjoc.12.44

Graphical Abstract
  • Sciences) for the discovery of the terpenoid antimalaria drug artemisinin that is produced by the plant Artemisia annua [3], and to Satoshi Õmura and William C. Campbell for the discovery of avermectins isolated from the actinobacterium Streptomyces avermitilis at the famous Kitasato Institute and for the
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Editorial
Published 03 Mar 2016

Recent highlights in biosynthesis research using stable isotopes

  • Jan Rinkel and
  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2015, 11, 2493–2508, doi:10.3762/bjoc.11.271

Graphical Abstract
  • products and are remarkably diverse in structure, bioactivity, and use. Prominent examples such as the antimalaria drug artemisinin (28) from Artemisia annua, ingenol (29) and its derivatives from Euphorbia ingens [56], or the anticancer drug paclitaxel (30) feature highly functionalized polycyclic carbon
  • stereocenters deduced from labeling experiments. Structure of thiomarinol A (27). Bold bonds indicate carbon atoms derived from 4-hydroxybutyrate. Structures of artemisinin (28), ingenol (29) and paclitaxel (30). The revised (31) and the previously suggested (32) structure of hypodoratoxide and the structure of
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Published 09 Dec 2015

Pyridinoacridine alkaloids of marine origin: NMR and MS spectral data, synthesis, biosynthesis and biological activity

  • Louis P. Sandjo,
  • Victor Kuete and
  • Maique W. Biavatti

Beilstein J. Org. Chem. 2015, 11, 1667–1699, doi:10.3762/bjoc.11.183

Graphical Abstract
  • subtilis, giving a MIC of 3.1 µg/mL [87]. 42 displayed in vitro antiparasitic activity against Plasmodium falciparum (K1, NF54), Leshmania donovani, Trypanosoma cruzi and T. rhodesiense but the effect was much lower than that of standard drugs artemisinin and chloroquine [88]. Ascididemin (42) displayed
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Published 18 Sep 2015

The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry

  • Marcus Baumann and
  • Ian R. Baxendale

Beilstein J. Org. Chem. 2015, 11, 1194–1219, doi:10.3762/bjoc.11.134

Graphical Abstract
  • reaction conditions are mandatory in order to succeed. The flow synthesis of the high profile antimalaria agent artemisinin (55) was reported by the Seeberger group in 2012 [61][62]. This intriguing approach represents one of the few examples where photochemistry has been employed in the synthesis of a
  • pharmaceutical. For this endeavour dihydroartimisinic acid (56), an advanced building block that is available via chemoselective batch reduction of bioengineered artemisinic acid (57), was chosen as the starting point. The key transformations to yield artemisinin thus demanded a reaction cascade including a
  • to enable the remaining reaction cascade to take place in a subsequent thermal reactor unit. After off-line purification by silica gel chromatography and crystallisation artemisinin was isolated in 39% yield equating to an extrapolated productivity of approximately 200 g per day. More recently
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Published 17 Jul 2015

Cyclization–endoperoxidation cascade reactions of dienes mediated by a pyrylium photoredox catalyst

  • Nathan J. Gesmundo and
  • David A. Nicewicz

Beilstein J. Org. Chem. 2014, 10, 1272–1281, doi:10.3762/bjoc.10.128

Graphical Abstract
  • bond engenders these compounds with a range of important biological functions, most notably, antimalarial and antitumor activity (e.g., artemisinin, yingzhaosu A and merulin C) [1][2][3][4]. From a synthetic standpoint, the installation of the endoperoxide moiety presents a significant challenge due to
  • its susceptibility to reduction and for this reason, is ideally introduced late-stage in target-oriented synthesis. Additionally, many endoperoxide natural products possess architecturally complex frameworks (e.g., artemisinin, yingzhaosu A, muurolan-4,7-peroxide) [5] that pose significant synthetic
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Published 03 Jun 2014

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

  • Alexander O. Terent'ev,
  • Dmitry A. Borisov,
  • Vera A. Vil’ and
  • Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

Graphical Abstract
  • considerable role. In medicinal chemistry of peroxides, artemisinin a natural peroxide exhibiting high antimalarial activity, is the most important drug in use for approximately 30 years. Artemisinin was isolated in 1971 from leaves of annual wormwood (Artemesia annua) [49][50][51]; the 1,2,4-trioxane ring V
  • is the key pharmacophore of these drugs. A series of semi-synthetic derivatives of artemisinin were synthesized: artesunate, artemether, and artemisone (Figure 2). Currently, drugs based on these compounds are considered as the most efficacious for the treatment of malaria [52][53][54][55][56][57][58
  • ][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76]. The discovery of arterolane, a synthetic 1,2,4-trioxolane, is a considerable success in the search for easily available synthetic peroxides capable of replacing artemisinin and its derivatives in medical practice. Currently
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Published 08 Jan 2014

Natural products in synthesis and biosynthesis

  • Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 1897–1898, doi:10.3762/bjoc.9.223

Graphical Abstract
  • examples of comparing natural to artificial systems it is their interplay that may provide the best solutions to some of the most urgent problems of our time. A perfect example is artemisinin, a terpenoid natural product from Artemisia annua, which is highly efficient in the treatment of malaria. The
  • ] and its further elaboration by chemical synthesis [7] procures sufficient quantities of artemisinin at a reasonable price. An impressive demonstration of the effectiveness of multi-disciplinary research. I would like to thank the highly professional team of the Beilstein-Institut for a very pleasant
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Published 19 Sep 2013

Flow photochemistry: Old light through new windows

  • Jonathan P. Knowles,
  • Luke D. Elliott and
  • Kevin I. Booker-Milburn

Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229

Graphical Abstract
  • , despite the reactor volume being only 285 µL [39]. This output was 2.6 times that of a 50 mL batch reactor. The same reactor was also successfully applied to the oxidation of allylic alcohols for the synthesis of the antimalarial artemisinin, and the conversion of α-terpinene to ascaridole. Addition of a
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Published 21 Nov 2012

Triple-channel microreactor for biphasic gas–liquid reactions: Photosensitized oxygenations

  • Ram Awatar Maurya,
  • Chan Pil Park and
  • Dong-Pyo Kim

Beilstein J. Org. Chem. 2011, 7, 1158–1163, doi:10.3762/bjoc.7.134

Graphical Abstract
  • efficiency of the triple-channel microreactor. The product of this reaction is an allyl hydroperoxide alcohol that is used in the synthesis of artemisinin-derived antimalarial 1,2,4-trioxanes [48]. The reaction in the triple-channel and in batch was carried out as aforementioned with methylene blue as
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Published 24 Aug 2011

Novel tetracyclic structures from the synthesis of thiolactone-isatin hybrids

  • Renate Hazel Hans,
  • Hong Su and
  • Kelly Chibale

Beilstein J. Org. Chem. 2010, 6, No. 78, doi:10.3762/bjoc.6.78

Graphical Abstract
  • natural and natural product-like hybrid constructs such as the artemisinin-quinine [2], nostocarboline-ciprofloxacin [3] and isatin-lamuvidine [4] (Figure 1). Interest in exploring this approach also derives from the pharmacophore-rich compound library it offers. This precludes the need for large
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Published 19 Jul 2010

Synthesis of spiroannulated and 3-arylated 1,2,4-trioxanes from mesitylol and methyl 4-hydroxytiglate by photooxygenation and peroxyacetalization

  • Axel G. Griesbeck,
  • Lars-Oliver Höinck and
  • Jörg M. Neudörfl

Beilstein J. Org. Chem. 2010, 6, No. 61, doi:10.3762/bjoc.6.61

Graphical Abstract
  • hydroperoxy alcohol 4 and benzaldehyde derivatives, was investigated by X-ray crystallography. Keywords: ene reaction; peracetalization; peroxides; singlet oxygen; trioxanes; Introduction The antimalaria-active molecule artemisinin (1) is a naturally occurring sesquiterpene peroxide with remarkable
  • pharmacological properties. Hydrophilic as well as lipophilic derivatives have been prepared from artemisinin and show improved antimalarial properties and better bioavailabilities [1][2][3][4][5]. In recent years, additional medicinal properties of artemisinin and the water soluble artesunates have been
  • might show promise in overcoming the forthcoming problem of artemisinin resistance [8]. From a synthetic point of view, the preparation of the pharmacophore, the central 1,2,4-trioxane ring system, is possible by a number of strategies [9][10]. We, for example, have previously reported the use of the
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Published 07 Jun 2010
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