Enantioselective synthesis of functionalized 2-oxo-cyclohexane carbonitriles. Access to a trioxane analogue of artemisinin

被引:13
作者
Hamzaoui, M
Provot, O
Gregoire, F
Riche, C
Chiaroni, A
Gay, F
Moskowitz, H
Mayrargue, J
机构
[1] UNIV PARIS 11, FAC PHARM, CNRS, CHIM ORGAN LAB, F-92290 CHATENAY MALABRY, FRANCE
[2] CNRS, INST CHIM SUBST NAT, F-91198 GIF SUR YVETTE, FRANCE
[3] HOP LA PITIE SALPETRIERE, SERV PARASITOL, LAB EPIDEMIOL & CHIMIORESISTANCE PALUDISME, F-75013 PARIS, FRANCE
关键词
D O I
10.1016/S0957-4166(97)00238-3
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Synthesis of optically active 2-oxo-1-alkylcyclohexane carbonitriles is described leading to access to a new bicyclic simplified analogue of artemisinin. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2085 / 2088
页数:4
相关论文
共 15 条
[1]   STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-ARTEMISININ, THE ANTIMALARIAL CONSTITUENT OF ARTEMISIA-ANNUA L [J].
AVERY, MA ;
CHONG, WKM ;
JENNINGSWHITE, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :974-979
[2]   SCOPE AND MECHANISM OF REACTION OF ALKYLIDENEPHOSPHORANES WITH NITRILES [J].
BARNHARD.RG ;
MCEWEN, WE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (26) :7009-+
[3]   A novel asymmetric total synthesis of (+)-artemisinin [J].
Constantino, MG ;
Beltrame, M ;
daSilva, GVJ .
SYNTHETIC COMMUNICATIONS, 1996, 26 (02) :321-329
[4]   THE ASYMMETRIC MICHAEL ADDITION-REACTIONS USING CHIRAL IMINES [J].
DANGELO, J ;
DESMAELE, D ;
DUMAS, F ;
GUINGANT, A .
TETRAHEDRON-ASYMMETRY, 1992, 3 (04) :459-505
[5]   THE ASYMMETRIC MICHAEL REACTION INVOLVING CHIRAL IMINES - USE OF ACRYLONITRILE AS ACCEPTOR AND SUBSEQUENT FUNCTIONALIZATION OF THE ADDUCTS [J].
DESMAELE, D ;
ZOUHIRI, F ;
DANGELO, J .
TETRAHEDRON-ASYMMETRY, 1994, 5 (09) :1645-1648
[6]  
ENDERS D, 1993, SYNTHESIS-STUTTGART, P725
[7]   SYNTHESIS, STRUCTURE, AND ANTIMALARIAL ACTIVITY OF TRICYCLIC 1,2,4-TRIOXANES RELATED TO ARTEMISININ [J].
JEFFORD, CW ;
VELARDE, JA ;
BERNARDINELLI, G ;
BRAY, DH ;
WARHURST, DC ;
MILHOUS, WK .
HELVETICA CHIMICA ACTA, 1993, 76 (08) :2775-2788
[8]   QINGHAOSU (ARTEMISININ) - AN ANTIMALARIAL DRUG FROM CHINA [J].
KLAYMAN, DL .
SCIENCE, 1985, 228 (4703) :1049-1055
[9]  
LIU HJ, 1993, TETRAHEDRON LETT, V34, P4435, DOI 10.1016/0040-4039(93)88052-K
[10]   ULTRASOUND IN ORGANIC-SYNTHESIS .5. PREPARATION AND SOME REACTIONS OF COLLOIDAL POTASSIUM [J].
LUCHE, JL ;
PETRIER, C ;
DUPUY, C .
TETRAHEDRON LETTERS, 1984, 25 (07) :753-756