Stereocontrolled cyclopropanation of Garner's aldehyde derived enones

被引:19
作者
Ma, DW
Jiang, YW
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
关键词
D O I
10.1016/S0957-4166(00)00327-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction of sulfonium ylides with enones 5 derived from (S)-Garner's aldehyde in toluene provides 1,2,3-trisubstituted cyclopropanes. The configuration of the major isomer is 2R,1'R,2'R,3'R. Using this reaction a 3-benzyl analogue of the CCG family compounds was synthesized. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3727 / 3736
页数:10
相关论文
共 16 条
[11]   SYNTHESIS OF L-2-(2,3-DICARBOXYCYCLOPROPYL)GLYCINES - NOVEL CONFORMATIONALLY RESTRICTED GLUTAMATE ANALOGS [J].
OHFUNE, Y ;
SHIMAMOTO, K ;
ISHIDA, M ;
SHINOZAKI, H .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (01) :15-18
[12]   Synthesis and pharmacological characterization of all sixteen stereoisomers of 2-(2'-carboxy-3'-phenylcyclopropyl)glycine. Focus on (2S,1'S,2'S,3'R)-2-(2'-carboxy-3'-phenylcyclopropyl)glycine, a novel and selective group II metabotropic glutamate receptors antagonist [J].
Pellicciari, R ;
Marinozzi, M ;
Natalini, B ;
Costantino, G ;
Luneia, R ;
Giorgi, G ;
Moroni, F ;
Thomsen, C .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (11) :2259-2269
[13]  
PELLICCIARI R, 1999, J MED CHEM, V42, P2259
[14]   ENANTIOSELECTIVE SYNTHESIS OF (+)-PRESQUALENE DIPHOSPHATE [J].
ROGERS, DH ;
YI, EC ;
POULTER, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (04) :941-945
[15]   Syntheses and conformational analyses of glutamate analogs: 2-(2-Carboxy-3-substituted-cyclopropyl) glycines as useful probes for excitatory amino acid receptors [J].
Shimamoto, K ;
Ohfune, Y .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (02) :407-423
[16]   Structural diversity based on cyclopropane scaffolds [J].
Taylor, RE ;
Schmitt, MJ ;
Yuan, HQ .
ORGANIC LETTERS, 2000, 2 (05) :601-603