Literature DB >> 25991527

Applying green chemistry to the photochemical route to artemisinin.

Zacharias Amara1, Jessica F B Bellamy1, Raphael Horvath1, Samuel J Miller1, Andrew Beeby2, Andreas Burgard3, Kai Rossen3, Martyn Poliakoff1, Michael W George4.   

Abstract

Artemisinin is an important antimalarial drug, but, at present, the environmental and economic costs of its semi-synthetic production are relatively high. Most of these costs lie in the final chemical steps, which follow a complex acid- and photo-catalysed route with oxygenation by both singlet and triplet oxygen. We demonstrate that applying the principles of green chemistry can lead to innovative strategies that avoid many of the problems in current photochemical processes. The first strategy combines the use of liquid CO2 as solvent and a dual-function solid acid/photocatalyst. The second strategy is an ambient-temperature reaction in aqueous mixtures of organic solvents, where the only inputs are dihydroartemisinic acid, O2 and light, and the output is pure, crystalline artemisinin. Everything else-solvents, photocatalyst and aqueous acid-can be recycled. Some aspects developed here through green chemistry are likely to have wider application in photochemistry and other reactions.

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Year:  2015        PMID: 25991527     DOI: 10.1038/nchem.2261

Source DB:  PubMed          Journal:  Nat Chem        ISSN: 1755-4330            Impact factor:   24.427


  17 in total

Review 1.  Evaluating the "greenness" of chemical processes and products in the pharmaceutical industry--a green metrics primer.

Authors:  Concepción Jiménez-González; David J C Constable; Celia S Ponder
Journal:  Chem Soc Rev       Date:  2011-11-11       Impact factor: 54.564

2.  Continuous-flow synthesis of the anti-malaria drug artemisinin.

Authors:  François Lévesque; Peter H Seeberger
Journal:  Angew Chem Int Ed Engl       Date:  2012-01-16       Impact factor: 15.336

3.  Maximising the efficiency of continuous photo-oxidation with singlet oxygen in supercritical CO2 by use of fluorous biphasic catalysis.

Authors:  Jessica F B Hall; Xue Han; Martyn Poliakoff; Richard A Bourne; Michael W George
Journal:  Chem Commun (Camb)       Date:  2012-02-17       Impact factor: 6.222

4.  THE PHOTOCHEMISTRY OF THE FUTURE.

Authors:  G Ciamician
Journal:  Science       Date:  1912-09-27       Impact factor: 47.728

Review 5.  Industrial natural product chemistry for drug discovery and development.

Authors:  Armin Bauer; Mark Brönstrup
Journal:  Nat Prod Rep       Date:  2014-01       Impact factor: 13.423

Review 6.  Semi-synthetic artemisinin: a model for the use of synthetic biology in pharmaceutical development.

Authors:  Chris J Paddon; Jay D Keasling
Journal:  Nat Rev Microbiol       Date:  2014-04-01       Impact factor: 60.633

7.  Conversion of antimalarial drug artemisinin to a new series of tricyclic 1,2,4-trioxanes1.

Authors:  Chandan Singh; Sandeep Chaudhary; Rani Kanchan; Sunil K Puri
Journal:  Org Lett       Date:  2007-09-18       Impact factor: 6.005

8.  A continuous-flow process for the synthesis of artemisinin.

Authors:  Daniel Kopetzki; François Lévesque; Peter H Seeberger
Journal:  Chemistry       Date:  2013-03-20       Impact factor: 5.236

Review 9.  Qinghaosu (artemisinin): an antimalarial drug from China.

Authors:  D L Klayman
Journal:  Science       Date:  1985-05-31       Impact factor: 47.728

10.  Cleaner continuous photo-oxidation using singlet oxygen in supercritical carbon dioxide.

Authors:  Richard A Bourne; Xue Han; Martyn Poliakoff; Michael W George
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

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  17 in total

1.  Manufacturing chemicals with light: any role in the circular economy?

Authors:  M Poliakoff; M W George
Journal:  Philos Trans A Math Phys Eng Sci       Date:  2020-07-06       Impact factor: 4.226

Review 2.  Heterogeneous photocatalysis in flow chemical reactors.

Authors:  Christopher G Thomson; Ai-Lan Lee; Filipe Vilela
Journal:  Beilstein J Org Chem       Date:  2020-06-26       Impact factor: 2.883

Review 3.  Rearrangements of organic peroxides and related processes.

Authors:  Ivan A Yaremenko; Vera A Vil'; Dmitry V Demchuk; Alexander O Terent'ev
Journal:  Beilstein J Org Chem       Date:  2016-08-03       Impact factor: 2.883

4.  The gal80 Deletion by CRISPR-Cas9 in Engineered Saccharomyces cerevisiae Produces Artemisinic Acid Without Galactose Induction.

Authors:  Limei Ai; Weiwei Guo; Wei Chen; Yun Teng; Liping Bai
Journal:  Curr Microbiol       Date:  2019-08-07       Impact factor: 2.188

Review 5.  Continuous Photo-Oxidation in a Vortex Reactor: Efficient Operations Using Air Drawn from the Laboratory.

Authors:  Darren S Lee; Zacharias Amara; Charlotte A Clark; Zeyuan Xu; Bruce Kakimpa; Herve P Morvan; Stephen J Pickering; Martyn Poliakoff; Michael W George
Journal:  Org Process Res Dev       Date:  2017-07-03       Impact factor: 3.317

6.  A simplified and scalable synthesis of artesunate.

Authors:  Armin Presser; Andrea Feichtinger; Silke Buzzi
Journal:  Monatsh Chem       Date:  2016-12-02       Impact factor: 1.451

7.  Concise synthesis of artemisinin from a farnesyl diphosphate analogue.

Authors:  Xiaoping Tang; Melodi Demiray; Thomas Wirth; Rudolf K Allemann
Journal:  Bioorg Med Chem       Date:  2017-04-04       Impact factor: 3.641

8.  Cobalt-catalyzed highly enantioselective hydrogenation of α,β-unsaturated carboxylic acids.

Authors:  Xiaoyong Du; Ye Xiao; Jia-Ming Huang; Yao Zhang; Ya-Nan Duan; Heng Wang; Chuan Shi; Gen-Qiang Chen; Xumu Zhang
Journal:  Nat Commun       Date:  2020-06-26       Impact factor: 14.919

9.  Chemo- and Diastereoselective Hydrosilylation of Amorphadiene toward the Synthesis of Artemisinin.

Authors:  Geoffrey Schwertz; Andrea Zanetti; Marllon Nascimento de Oliveira; Mario Andrés Gomez Fernandez; Zacharias Amara; Janine Cossy
Journal:  J Org Chem       Date:  2020-07-09       Impact factor: 4.354

Review 10.  Synthetic Strategies for Peroxide Ring Construction in Artemisinin.

Authors:  Vera A Vil'; Ivan A Yaremenko; Alexey I Ilovaisky; Alexander O Terent'ev
Journal:  Molecules       Date:  2017-01-11       Impact factor: 4.411

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