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Chemistry - A European Journal

Volumn 19, Issue 17, 2013, Pages 5450-5456

A continuous-flow process for the synthesis of artemisinin

(3) Kopetzki, Daniel a Lévesque, François a Seeberger, Peter H a,b

a MAX PLANCK INSTITUTE OF COLLOIDS AND INTERFACES (Germany)

b FREIE UNIVERSITÄT BERLIN (Germany)

Author keywords

antimalarial agents; artemisinin; flow chemistry; photochemistry; singlet oxygen

Indexed keywords

ANTIMALARIAL AGENT; ANTIMALARIAL DRUG; ARTEMISINIC ACID; ARTEMISININ; BIOLOGICAL PRECURSORS; CONTINUOUS-FLOW PROCESS; FLOW CHEMISTRY; SINGLET OXYGEN;

CHEMISTRY; PHOTOCHEMICAL REACTIONS; SYNTHESIS (CHEMICAL);

OXYGEN;

ANTIMALARIAL AGENT; ARTEMISINIC ACID; ARTEMISININ; ARTEMISININ DERIVATIVE; DIHYDROARTEMISINIC ACID; SINGLET OXYGEN;

AFRICA; ARTEMISIA; ARTICLE; CHEMISTRY; SYNTHESIS;

AFRICA; ANTIMALARIALS; ARTEMISIA; ARTEMISININS; SINGLET OXYGEN;

EID: 84876208897 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.201204558 Document Type: Article

Times cited : (199)

References (48)

1
- 84856408211
- World Health Organization, Geneva
- World Malaria Report, World Health Organization, Geneva, 2011.
- (2011) World Malaria Report

2
- 23944451082
- T. K. Mutabingwa, Acta Trop. 2005, 95, 305-315.
- (2005) Acta Trop. , vol.95 , pp. 305-315
- Mutabingwa, T.K.¹

3
- 80053976628
- Y. Tu, Nat. Med. 2011, 17, 1217-1220.
- (2011) Nat. Med. , vol.17 , pp. 1217-1220
- Tu, Y.¹

4
- 0029995163
- G. H. Posner, S. B. Park, L. Gonzalez, D. Wang, J. N. Cumming, D. Klinedinst, T. A. Shapiro, M. D. Bachi, J. Am. Chem. Soc. 1996, 118, 3537-3538.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 3537-3538
- Posner, G.H.¹ Park, S.B.² Gonzalez, L.³ Wang, D.⁴ Cumming, J.N.⁵ Klinedinst, D.⁶ Shapiro, T.A.⁷ Bachi, M.D.⁸

5
- 0141988634
- Y. Li, Y. L. Wu, Curr. Med. Chem. 2003, 10, 2197-2230
- (2003) Curr. Med. Chem. , vol.10 , pp. 2197-2230
- Li, Y.¹ Wu, Y.L.²

6
- 33646158237
- R. K. Haynes, Curr. Top. Med. Chem. 2006, 6, 509-537
- (2006) Curr. Top. Med. Chem. , vol.6 , pp. 509-537
- Haynes, R.K.¹

7
- 84859010979
- A. R. Kreeftmeijer-Vegter, P. J. van Genderen, L. G. Visser, W. F.-W Bierman, J. Clerinx, C. K.-W van Veldhuizen, P. J. de Vries, Malar. J. 2012, 11, 102.
- (2012) Malar. J. , vol.11 , pp. 102
- Kreeftmeijer-Vegter, A.R.¹ Van Genderen, P.J.² Visser, L.G.³ Bierman, W.F.-W.⁴ Clerinx, J.⁵ Van Veldhuizen, C.K.-W.⁶ De Vries, P.J.⁷

8
- 0020577131
- G. Schmid, W. Hofheinz, J. Am. Chem. Soc. 1983, 105, 624-625
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 624-625
- Schmid, G.¹ Hofheinz, W.²

9
- 0027291372
- H. J. Liu, W. L. Yeh, S. Y. Chew, Tetrahedron Lett. 1993, 34, 4435-4438
- (1993) Tetrahedron Lett. , vol.34 , pp. 4435-4438
- Liu, H.J.¹ Yeh, W.L.² Chew, S.Y.³

10
- 76449102123
- J. S. Yadav, B. Thirupathaiah, P. Srihari, Tetrahedron 2010, 66, 2005-2009
- (2010) Tetrahedron , vol.66 , pp. 2005-2009
- Yadav, J.S.¹ Thirupathaiah, B.² Srihari, P.³

11
- 84865444062
- C. Zhu, S. P. Cook, J. Am. Chem. Soc. 2012, 134, 13577-13579
- (2012) J. Am. Chem. Soc. , vol.134 , pp. 13577-13579
- Zhu, C.¹ Cook, S.P.²

12
- 62149145855
- X. X. Xu, J. Zhu, D. Z. Huang, W. S. Zhou, Tetrahedron 1986, 42, 819-828.
- (1986) Tetrahedron , vol.42 , pp. 819-828
- Xu, X.X.¹ Zhu, J.² Huang, D.Z.³ Zhou, W.S.⁴

13
- 77955491116
- R. van Noorden, Nature 2010, 466, 672-673
- (2010) Nature , vol.466 , pp. 672-673
- Van Noorden, R.¹

14
- 84864299337
- A. Maxmen, Nat. Med. 2012, 18, 634-635.
- (2012) Nat. Med. , vol.18 , pp. 634-635
- Maxmen, A.¹

15
- 78649475176
- G. D. Brown, Molecules 2010, 15, 7603-7698
- (2010) Molecules , vol.15 , pp. 7603-7698
- Brown, G.D.¹

16
- 0001815264
- R. K. Haynes, S. C. Vonwiller, Acc. Chem. Res. 1997, 30, 73-79.
- (1997) Acc. Chem. Res. , vol.30 , pp. 73-79
- Haynes, R.K.¹ Vonwiller, S.C.²

17
- 0037185534
- L. K. Sy, G. D. Brown, Tetrahedron 2002, 58, 897-908.
- (2002) Tetrahedron , vol.58 , pp. 897-908
- Sy, L.K.¹ Brown, G.D.²

18
- 56549084929
- P. S. Covello, Phytochemistry 2008, 69, 2881-2885.
- (2008) Phytochemistry , vol.69 , pp. 2881-2885
- Covello, P.S.¹

19
- 0024429567
- R. J. Roth, N. Acton, J. Nat. Prod. 1989, 52, 1183-1185
- (1989) J. Nat. Prod. , vol.52 , pp. 1183-1185
- Roth, R.J.¹ Acton, N.²

20
- 0025269828
- R. K. Haynes, S. C. Vonwiller, J. Chem. Soc., Chem. Commun. 1990, 451-453.
- (1990) J. Chem. Soc., Chem. Commun. , pp. 451-453
- Haynes, R.K.¹ Vonwiller, S.C.²

21
- 0033983929
- T. E. Wallaart, N. Pras, A. C. Beekman, W. J. Quax, Planta Med. 2000, 66, 57-62
- (2000) Planta Med. , vol.66 , pp. 57-62
- Wallaart, T.E.¹ Pras, N.² Beekman, A.C.³ Quax, W.J.⁴

22
- 0028178706
- H. J. Woerdenbag, N. Pras, N. G. Chan, B. T. Bang, R. Bos, W. Vanuden, P. V. Y. N. V. Boi, S. Batterman, C. B. Lugt, Planta Med. 1994, 60, 272-275.
- (1994) Planta Med. , vol.60 , pp. 272-275
- Woerdenbag, H.J.¹ Pras, N.² Chan, N.G.³ Bang, B.T.⁴ Bos, R.⁵ Vanuden, W.⁶ Boi, P.V.Y.N.V.⁷ Batterman, S.⁸ Lugt, C.B.⁹

23
- 0001500832
- M. Jung, H. N. Elsohly, E. M. Croom, A. T. McPhail, D. R. McPhail, J. Org. Chem. 1986, 51, 5417-5419.
- (1986) J. Org. Chem. , vol.51 , pp. 5417-5419
- Jung, M.¹ Elsohly, H.N.² Croom, E.M.³ McPhail, A.T.⁴ McPhail, D.R.⁵

24
- 0035214418
- N. Delabays, X. Simonnet, M. Gaudin, Curr. Med. Chem. 2001, 8, 1795-1801.
- (2001) Curr. Med. Chem. , vol.8 , pp. 1795-1801
- Delabays, N.¹ Simonnet, X.² Gaudin, M.³

25
- 76449113389
- J. F. S. Ferreira, D. L. Luthria, J. Agric. Food Chem. 2010, 58, 1691-1698
- (2010) J. Agric. Food Chem. , vol.58 , pp. 1691-1698
- Ferreira, J.F.S.¹ Luthria, D.L.²

26
- 34548656600
- W. J. M. Lommen, S. Elzinga, F. W. A. Verstappen, H. J. Bouwmeester, Planta Med. 2007, 73, 1133-1139.
- (2007) Planta Med. , vol.73 , pp. 1133-1139
- Lommen, W.J.M.¹ Elzinga, S.² Verstappen, F.W.A.³ Bouwmeester, H.J.⁴

27
- 33645870422
- D. K. Ro, E. M. Paradise, M. Ouellet, K. J. Fisher, K. L. Newman, J. M. Ndungu, K. A. Ho, R. A. Eachus, T. S. Ham, J. Kirby, M. C. Y. Chang, S. T. Withers, Y. Shiba, R. Sarpong, J. D. Keasling, Nature 2006, 440, 940-943.
- (2006) Nature , vol.440 , pp. 940-943
- Ro, D.K.¹ Paradise, E.M.² Ouellet, M.³ Fisher, K.J.⁴ Newman, K.L.⁵ Ndungu, J.M.⁶ Ho, K.A.⁷ Eachus, R.A.⁸ Ham, T.S.⁹ Kirby, J.¹⁰ Chang, M.C.Y.¹¹ Withers, S.T.¹² Shiba, Y.¹³ Sarpong, R.¹⁴ Keasling, J.D.¹⁵

28
- 84876265228
- (Sanofi-Aventis, Fr.), WO 2011/026865
- J. Dhainaut, A. Dlubala, R. Guevel, A. Medard, G. Oddon, N. Raymond, J. Turconi, (Sanofi-Aventis, Fr.), WO 2011/026865, 2011
- (2011)
- Dhainaut, J.¹ Dlubala, A.² Guevel, R.³ Medard, A.⁴ Oddon, G.⁵ Raymond, N.⁶ Turconi, J.⁷

29
- 84876245713
- (Sanofi-Aventis, Fr.), WO 2011/030223.
- V. Kraft, G. Kretzschmar, K. Rossen, (Sanofi-Aventis, Fr.), WO 2011/030223, 2011.
- (2011)
- Kraft, V.¹ Kretzschmar, G.² Rossen, K.³

30
- 52049090608
- Y. Zhang, K. H. Teoh, D. W. Reed, L. Maes, A. Goossens, D. J. H. Olson, A. R. S. Ross, P. S. Covello, J. Biol. Chem. 2008, 283, 21501-21508
- (2008) J. Biol. Chem. , vol.283 , pp. 21501-21508
- Zhang, Y.¹ Teoh, K.H.² Reed, D.W.³ Maes, L.⁴ Goossens, A.⁵ Olson, D.J.H.⁶ Ross, A.R.S.⁷ Covello, P.S.⁸

31
- 84856389651
- P. J. Westfall, D. J. Pitera, J. R. Lenihan, D. Eng, F. X. Woolard, R. Regentin, T. Horning, H. Tsuruta, D. J. Melis, A. Owens, S. Fickes, D. Diola, K. R. Benjamin, J. D. Keasling, M. D. Leavell, D. J. McPhee, N. S. Renninger, J. D. Newman, C. J. Paddon, Proc. Natl. Acad. Sci. USA 2012, 109, E 111 -E 118.
- (2012) Proc. Natl. Acad. Sci. USA , vol.109
- Westfall, P.J.¹ Pitera, D.J.² Lenihan, J.R.³ Eng, D.⁴ Woolard, F.X.⁵ Regentin, R.⁶ Horning, T.⁷ Tsuruta, H.⁸ Melis, D.J.⁹ Owens, A.¹⁰ Fickes, S.¹¹ Diola, D.¹² Benjamin, K.R.¹³ Keasling, J.D.¹⁴ Leavell, M.D.¹⁵ McPhee, D.J.¹⁶ Renninger, N.S.¹⁷ Newman, J.D.¹⁸ Paddon, C.J.¹⁹

32
- 0036838398
- M. C. DeRosa, R. J. Crutchley, Coord. Chem. Rev. 2002, 233, 351-371.
- (2002) Coord. Chem. Rev. , vol.233 , pp. 351-371
- Derosa, M.C.¹ Crutchley, R.J.²

33
- 24944575233
- B. D. A. Hook, W. Dohle, P. R. Hirst, M. Pickworth, M. B. Berry, K. I. Booker-Milburn, J. Org. Chem. 2005, 70, 7558-7564.
- (2005) J. Org. Chem. , vol.70 , pp. 7558-7564
- Hook, B.D.A.¹ Dohle, W.² Hirst, P.R.³ Pickworth, M.⁴ Berry, M.B.⁵ Booker-Milburn, K.I.⁶

34
- 4043080112
- K. Jähnisch, V. Hessel, H. Lowe, M. Baerns, Angew. Chem. 2004, 116, 410-451
- (2004) Angew. Chem. , vol.116 , pp. 410-451
- Jähnisch, K.¹ Hessel, V.² Lowe, H.³ Baerns, M.⁴

35
- 17344391357
- Angew. Chem. Int. Ed. 2004, 43, 406-446.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 406-446

36
- 0036304954
- R. C. R. Wootton, R. Fortt, A. J. de Mello, Org. Process Res. Dev. 2002, 6, 187-189
- (2002) Org. Process Res. Dev. , vol.6 , pp. 187-189
- Wootton, R.C.R.¹ Fortt, R.² De Mello, A.J.³

37
- 80054728059
- F. Lévesque, P. H. Seeberger, Org. Lett. 2011, 13, 5008-5011
- (2011) Org. Lett. , vol.13 , pp. 5008-5011
- Lévesque, F.¹ Seeberger, P.H.²

38
- 82955185735
- R. A. Bourne, X. Han, M. Poliakoff, M. W. George, Angew. Chem. 2009, 121, 5426-5429
- (2009) Angew. Chem. , vol.121 , pp. 5426-5429
- Bourne, R.A.¹ Han, X.² Poliakoff, M.³ George, M.W.⁴

39
- 70349931208
- Angew. Chem. Int. Ed. 2009, 48, 5322-5325.
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5322-5325

40
- 84857029523
- F. Lévesque, P. H. Seeberger, Angew. Chem. Int. Ed. 2012, 51, 1706-1709.
- (2012) Angew. Chem. Int. Ed. , vol.51 , pp. 1706-1709
- Lévesque, F.¹ Seeberger, P.H.²

41
- 84876263020
- (Dragoco Gerberding & Co. AG, Germany), US 005892059 A
- W. Pickenhagen, D. Schatkowski, (Dragoco Gerberding & Co. AG, Germany), US 005892059 A, 1999.
- (1999)
- Pickenhagen, W.¹ Schatkowski, D.²

42
- 84859305057
- F. R. Bou-Hamdan, P. H. Seeberger, Chem. Sci. 2012, 3, 1612-1616.
- (2012) Chem. Sci. , vol.3 , pp. 1612-1616
- Bou-Hamdan, F.R.¹ Seeberger, P.H.²

43
- 0000355776
- R. C. Kanner, C. S. Foote, J. Am. Chem. Soc. 1992, 114, 678-681.
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 678-681
- Kanner, R.C.¹ Foote, C.S.²

44
- 0034298126
- V. S. Chirvony, A. van Hoek, V. A. Galievsky, I. V. Sazanovich, T. J. Schaafsma, D. Holten, J. Phys. Chem. B 2000, 104, 9909-9917.
- (2000) J. Phys. Chem. B , vol.104 , pp. 9909-9917
- Chirvony, V.S.¹ Van Hoek, A.² Galievsky, V.A.³ Sazanovich, I.V.⁴ Schaafsma, T.J.⁵ Holten, D.⁶

45
- 0028812746
- S. C. Vonwiller, J. A. Warner, S. T. Mann, R. K. Haynes, J. Am. Chem. Soc. 1995, 117, 11098-11105.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 11098-11105
- Vonwiller, S.C.¹ Warner, J.A.² Mann, S.T.³ Haynes, R.K.⁴

46
- 80052092997
- R. W. Stringham, M. Pennell, W. Cabri, G. Carzana, F. Giorgi, S. Lalli, G. Marazzi, M. Torri, J. Chromatogr. A 2011, 1218, 6838-6842.
- (2011) J. Chromatogr. A , vol.1218 , pp. 6838-6842
- Stringham, R.W.¹ Pennell, M.² Cabri, W.³ Carzana, G.⁴ Giorgi, F.⁵ Lalli, S.⁶ Marazzi, G.⁷ Torri, M.⁸

47
- 0032944335
- T. E. Wallaart, W. van Uden, H. G. M. Lubberink, H. J. Woerdenbag, N. Pras, W. J. Quax, J. Nat. Prod. 1999, 62, 430-433
- (1999) J. Nat. Prod. , vol.62 , pp. 430-433
- Wallaart, T.E.¹ Van Uden, W.² Lubberink, H.G.M.³ Woerdenbag, H.J.⁴ Pras, N.⁵ Quax, W.J.⁶

48
- 0028283056
- R. K. Haynes, S. C. Vonwiller, Trans. R. Soc. Trop. Med. Hyg. 1994, 88, 23-26.
- (1994) Trans. R. Soc. Trop. Med. Hyg. , vol.88 , pp. 23-26
- Haynes, R.K.¹ Vonwiller, S.C.²

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