Stereochemically controlled cyclopropanation of (S)-glyceraldehyde acetonide-derived olefins.: Synthesis of (2S,1′R,2′R,3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine

被引:29
作者
Ma, DW
Cao, YY
Yang, Y
Cheng, DL
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bioorgan & Nat Prod Chem, Shanghai 200032, Peoples R China
[2] Lanzhou Univ, Dept Chem, Lanzhou 730000, Peoples R China
关键词
D O I
10.1021/ol990598j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The reactions of ethyl (dimethylsulfuranylidene)acetate or other related sulfonium ylides with olefins 1 derived from (S)-glyceraldehyde acetonide provide cyclopropanation products in good to excellent diastereoselectivity. On the basis of this reaction, a new synthetic protocol for (2S,1'R,2'R,3'R)-2-(2',3'-dicarboxycyclopropyl)glycine (L-DCG-IV), an isotype-selective agonist of metabotropic glutamate receptors, is developed.
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页码:285 / 287
页数:3
相关论文
共 26 条
[1]  
Braish TF, 1996, SYNLETT, P1100
[2]  
Bubert C, 1997, SYNLETT, P827
[3]  
BURGESS K, 1994, SYNLETT, P574
[4]   Stereoselective cyclopropanation of enones with ethyl dimethylsulfonium acetate bromide in the presence of DBU [J].
Collado, I ;
Dominguez, C ;
Ezquerra, J ;
Pedregal, C ;
Monn, JA .
TETRAHEDRON LETTERS, 1997, 38 (12) :2133-2136
[5]   DIMETHYLOXOSULFONIUM METHYLIDE ((CH3)2SOCH2) AND DIMETHYLSULFONIUM METHYLIDE ((CH3)2SCH2) FORMATION AND APPLICATION TO ORGANIC SYNTHESIS [J].
COREY, EJ ;
CHAYKOVSKY, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (06) :1353-+
[6]   New aspects of catalytic asymmetric cyclopropanation [J].
Doyle, MP ;
Protopopova, MN .
TETRAHEDRON, 1998, 54 (28) :7919-7946
[7]   PEROXYTRIFLUOROACETIC ACID .5. THE OXIDATION OF KETONES TO ESTERS [J].
EMMONS, WD ;
LUCAS, GB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (08) :2287-2288
[8]   The synthesis of enantiomerically pure, symmetrically substituted cyclopropane phosphonic acids - A constrained analog of the GABA antagonist phaclophen [J].
Hanessian, S ;
Cantin, LD ;
Roy, S ;
Andreotti, D ;
Gomtsyan, A .
TETRAHEDRON LETTERS, 1997, 38 (07) :1103-1106
[9]  
HUGHES DL, 1992, ORG REACTIONS, V42, P333
[10]   TOTAL SYNTHESIS OF NATURAL AMBRUTICIN [J].
KENDE, AS ;
FUJII, Y ;
MENDOZA, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9645-9646