C-10-fluorinated derivatives of dihydroartemisinin:: difluoromethylene ketones

被引:24
作者
Chorki, F
Crousse, B
Bonnet-Delpon, D
Bégué, JP
Brigaud, T
Portella, C
机构
[1] Fac Pharm Chatenay Malabry, CNRS, BIOCIS, F-92296 Chatenay Malabry, France
[2] CNRS, F-51687 Reims 2, France
[3] Fac Sci, F-51687 Reims 2, France
关键词
D O I
10.1016/S0040-4039(00)02272-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Difluoroenoxysilanes, prepared from aromatic and heterocyclic ketones, reacted with dihydroartemisinin acetate in the presence of Lewis acid to provide in good to moderate yields the 10-substituted difluoromethylene ketones. The introduction of the difluoromethylketone moiety was accompanied by the epimerisation of C-9. Best results were obtained using SnCl4 as Lewis acid. (C) 2001 Published by Elsevier Science Ltd.
引用
收藏
页码:1487 / 1489
页数:3
相关论文
共 21 条
[1]   Synthesis and in vivo antimalarial activity of 12 alpha-trifluoromethyl-hydroartemisinin [J].
Abouabdellah, A ;
Begue, JP ;
BonnetDelpon, D ;
Gantier, JC ;
Nga, TTT ;
Thac, TD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (22) :2717-2720
[2]  
AGTMAEL MA, 1999, TIPS, V20, P200
[3]   Mg0-promoted selective C-F bond cleavage of trifluoromethyl ketones:: a convenient method for the synthesis of 2,2-difluoro enol silanes [J].
Amii, H ;
Kobayashi, T ;
Hatamoto, Y ;
Uneyama, K .
CHEMICAL COMMUNICATIONS, 1999, (14) :1323-1324
[4]   Mixed organofluorine-organosilicon chemistry .6. Synthesis of gem-difluoro-C-glycosides and C-disaccharides from acylsilanes and trifluoromethyltrimethylsilane. An exploratory study [J].
Brigaud, T ;
Lefebvre, O ;
PlantierRoyon, R ;
Portella, C .
TETRAHEDRON LETTERS, 1996, 37 (34) :6115-6116
[5]   SYNTHESIS OF DIFLUOROENOXYSILANES FROM ACYLSILANES AND TRIFLUOROMETHYLTRIMETHYLSILANE (TFMTMS) - DRAMATIC EFFECT OF THE CATALYTIC FLUORIDE SOURCE [J].
BRIGAUD, T ;
DOUSSOT, P ;
PORTELLA, C .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (18) :2117-2118
[6]   A NEW METHOD FOR THE PREPARATION OF ARTEETHER AND ITS C-9 EPIMER [J].
ELFERALY, FS ;
ALYAHYA, MA ;
ORABI, KY .
JOURNAL OF NATURAL PRODUCTS, 1992, 55 (07) :878-883
[7]  
Jefford CW, 2000, HELV CHIM ACTA, V83, P1239, DOI 10.1002/1522-2675(20000607)83:6&lt
[8]  
1239::AID-HLCA1239&gt
[9]  
3.0.CO
[10]  
2-S