On the C-2 epimerisation of kainoids

被引:8
作者
Klotz, P [1 ]
Mann, A [1 ]
机构
[1] Fac Pharm, Lab Pharmacochim Commun Cellulaire, UMR 7081, F-67401 Illkirch Graffenstaden, France
关键词
D O I
10.1016/S0040-4039(03)00077-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The conditions for the epimerisation at carbon C-2 of phenyl kainic acid esters 6 and 7 and cis-3-prolinoglutamic esters 10 were systematically addressed. We found that the use of KHMDS in THF gave improved results over the existing procedures. Some mechanistic aspects of this peculiar epimerisation are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1927 / 1930
页数:4
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共 41 条
[1]   Synthesis of a potent (±)-4-(2-hydroxyphenyl) analogue of the acromelic acids by dearomatising cyclisation of a lithiated N-p-methoxybenzyl-4-methoxy-l-naphthamide [J].
Ahmed, A ;
Bragg, RA ;
Clayden, J ;
Tchabanenko, K .
TETRAHEDRON LETTERS, 2001, 42 (20) :3407-3410
[2]   Parallel synthesis of novel heteroaromatic acromelic acid analogues from kainic acid [J].
Baldwin, JE ;
Fryer, AM ;
Pritchard, GJ .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (08) :2588-2596
[3]   Dearomatising cyclisation of lithiated l-naphthamides with a phenylglycinol-derived chiral auxiliary: asymmetric synthesis of an arylkainoid and a kainoid-like pyroglutamate [J].
Bragg, RA ;
Clayden, J ;
Bladon, M ;
Ichihara, O .
TETRAHEDRON LETTERS, 2001, 42 (20) :3411-3414
[4]   Efficient radical cyclisation of secondary amides: An enantioselective synthesis of phenyl allokainoid [J].
Bryans, JS ;
Large, JM ;
Parsons, AF .
TETRAHEDRON LETTERS, 1999, 40 (17) :3487-3490
[5]   Efficient tin hydride-mediated radical cyclisation of secondary amides leading to substituted pyrrolidinones. Part 2. Application to the synthesis of aromatic kainic acid analogues [J].
Bryans, JS ;
Large, JM ;
Parsons, AF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (20) :2905-2910
[6]   The stereoselective preparation of substituted pyrrolidines using titanium- and zirconium-mediated diene metallabicyclisation methodology:: the total synthesis of (-)-α-kainic acid [J].
Campbell, AD ;
Raynham, TM ;
Taylor, RJK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (19) :3194-3204
[7]   Stereoselective synthesis of conformationally restricted analogues of aspartic and glutamic acids from endocyclic enecarbamates. [J].
Carpes, MJS ;
Miranda, PCML ;
Correia, CRD .
TETRAHEDRON LETTERS, 1997, 38 (11) :1869-1872
[8]   A stereodivergent approach to (-)-α-kainic acid and (+)-α-allokainic acid utilizing the complementarity of alkyne and allene cyclizations [J].
Chevliakov, MV ;
Montgomery, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (48) :11139-11143
[9]   Synthesis of (-)-kainic acid using chiral lithium amides in an asymmetric dearomatizing cyclization [J].
Clayden, J ;
Menet, CJ ;
Tchabanenko, K .
TETRAHEDRON, 2002, 58 (23) :4727-4733
[10]   Asymmetric deprotonation and dearomatising cyclisation of N-benzyl benzamides using chiral lithium amides:: formal synthesis of (-)-kainic acid [J].
Clayden, J ;
Menet, CJ ;
Mansfield, DJ .
CHEMICAL COMMUNICATIONS, 2002, (01) :38-39