Asymmetric syntheses of enantiomeric 3-p-fluorophenyl 1,2,4-trioxane analogues of the antimalarial artemisinin

Tetrahedron Letters

Volumn 40, Issue 51, 1999, Pages 9133-9136

  O' Neill, Paul M ^a   Miller, Alison ^a   Bickley, Jamie F ^a   Scheinmann, Feodor ^b   Oh, Chang Ho ^c,d   Posner, Gary H ^c  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b Ultrafine UFC Ltd   (United Kingdom)

^c JOHNS HOPKINS UNIVERSITY   (United States)

^d Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 TRIOXANE DERIVATIVE; ANTIMALARIAL AGENT; ARTEMISININ; MAGNESIUM CHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033579579     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01892-4     Document Type: Article

References (10)

1. TDK 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. Cumming, J.N.; Ploypradith, P.; Posner, G.H. Adv. Pharmacol.1997, 37, 253.
4. Posner, G.H.; Cumming, J.N.; Woo, S.-H.; Ploypradith, P.; Xie, S.; Shapiro, T.A., J. Med. Chem., 1998, 41, 940.
5. 5. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, L. Tetrahedron Asymm., 1997, 8, 2085. For an investigation of the effects of chemical substitution at the C-5a position of artemisinin tricyclic analogues see; Zouhiri, F.; Desmaële, D.; D'Angelo, J.; Riche, C.; Gay, F.; Cicéron, L. Tetrahedron Lett., 1998, 39, 2969.
6. Hamzaoui, M.; Provot, O.; Grégoire, F.; Riche, C; Chiaroni, A.; Gay, F.; Moskowitz, H.; Mayrargue, L. Tetrahedron Asymm., 1997, 8, 2085. For an investigation of the effects of chemical substitution at the C-5a position of artemisinin tricyclic analogues see; Zouhiri, F.; Desmaële, D.; D'Angelo, J.; Riche, C.; Gay, F.; Cicéron, L. Tetrahedron Lett., 1998, 39, 2969.
7. Hiroi, K.; Achiwa, K.; Yamada, S. Chem. Pharm. Bull., 1972, 20, 246.
8. Ito, Y.; Sawamura, M.; Kominami, K.; Saegusa, T.,Tetrahedron Lett.; 1985, 26, 5303.
9. 4F requires C = 66.22, H= 6.86, found C= 66.21, H= 6.88
10. 3. A total of 8313 reflections were collected in the range 2.24° to 22.50°. Lorentz and polarization but not absorption co-efficients were applied. The structure was solved by direct methods (SHEXS- 86). R1 = 0.0291, wR2 = 0.0697