Application of the TMSOTf-AgClO4 activator system to the synthesis of novel, potent, C-10 phenoxy derivatives of dihydroartemisinin

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 9129-9132

  O' Neill, Paul M ^a   Miller, Alison ^a   Ward, Stephen A ^a   Kevin Park, B ^a   Scheinmann, Feodor ^b   Stachulski, Andrew V ^b  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b Ultrafine UFC Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DIHYDROARTEMISININ DERIVATIVE; REAGENT;

ANTIMALARIAL ACTIVITY; ARTICLE; CHEMICAL MODIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NONHUMAN; PLASMODIUM FALCIPARUM; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

PLASMODIUM FALCIPARUM; PROTOZOA;

EID: 0033579650     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01891-2     Document Type: Article

References (19)

1. TDR News (News from the WHO Division of Control of Tropical Diseases) 1994, 46, 5.
2. Foley, M.; Tilley, L. Int. J. Parasitol. 1997, 27, 213.
3. Fishwick, J.; McClean, W.G.; Edwards, G.; Ward, S.A. Chem. Biol. Interact. 1995, 96, 263.
4. Grace, J.M.; Aguilar, A.J.; Trotman, K.M.; Brewer, T.G. Drug Metab. Disp. 1998, 26, 313.
5. Jung, M.; Lee, S. Heterocycles 1997, 45, 1055.
6. Haynes, R.K.; Vonwiller, S.C. Synlett 1992, 481.
7. Woo, S.H.; Parker, M.P.; Ploypradith, P.; Northrop, J.; Posner, G.H. Tetrahedron Lett. 1998, 39, 1533.
8. Jung, M. Bioorgan. Med. Chem. Lett. 1997, 7, 1091.
9. Lin, A.J.; Lee, M.; Klayman, D.L. J. Med. Chem., 1989, 32, 1249.
10. Varasi, M.; Walker, K.A.M.; Maddox, M.L. J. Org. Chem., 1987, 52, 4235.
11. Hughes, D.L.; Reamer, R.A.; Bergan, J.J.; Grabowski, E.J.J. J. Am. Chem. Soc. 1988, 110, 6487.
12. Woo, S.H.; Parker, N.P.; Ploypradith, P.; Northrop, J.; Posner, G.H. Tetrahedron Lett. 1998, 39, 1533.
13. Hosoya, T.; Takahiro, E.; Matsumoto, T.; Suzuki, K.J. Am. Chem. Soc. 1994, 116, 1004.
14. Postema, M.H.D. Tetrahedron, 1992, 48, 8545.
15. Matsumoto, T.; Hosoya, T; Suzuki, K. Tetrahedron Lett., 1990, 31, 4624.
16. Toshima, K.; Matsuo, G.; Tatsuta, K. Tetrahedron Lett. 1992, 33, 2175.
17. 2O, see ; Wang, D-Y.; Wu, Y.; Wu, Y-L.; Li, Y.; Shan, F. J. Chem. Soc., Perkin Trans. 1, 1999, 1827.
18. 5 requires 378.22805.
19. 3. A total of 2645 reflections were collected in the range 2.16° to 45°. Lorentz and polarization but not absorption co-efficients were applied. The structure was solved by direct methods (SHEXS- 86). R1 = 0.0272, wR2 = 0.0609