Conformationally constrained dipeptides.: Obtention of enantiomerically pure 6-acetamido-5-oxo-1,2,3,5,6,7-hexahydro-3-indolizine carboxylic acid

被引:9
作者
Millet, R
Meulon, E
Goossens, L
Houssin, R
Hénichart, JP
Rigo, B
机构
[1] Univ Lille 2, Inst Chim Pharmaceut Albert Lespagnol, F-59006 Lille, France
[2] Ecole Hautes Etud Ind, Lab Ingn Mol, F-59046 Lille, France
关键词
D O I
10.1002/jhet.5570370613
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The separation of a stereoisomeric mixture of esters 6, and the synthesis of the new enantiomerically pure unsaturated 6,5-fused bicyclic lactam 2 are described. The key-step involves trimethylsilyl iodide cleavage, without racemization, of a vinylogous carbamate. The cis N-acetylamino acid 2 is a new scaffold for the synthesis of rigid beta -turn mimetics.
引用
收藏
页码:1491 / 1494
页数:4
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共 40 条
[1]  
ADANG AEP, 1994, RECL TRAV CHIM PAY B, V113, P63
[2]   NaI/Me3SiCl -: a powerful tool for the development of one-pot reactions [J].
Arend, M .
JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (08) :760-763
[3]   CYCLIC BETA-ENAMINOESTERS DECARBOXYLATION WITH BORIC-ACID - A CONVENIENT SYNTHESIS OF CYCLIC IMINES [J].
BACOS, D ;
CELERIER, JP ;
LHOMMET, G .
TETRAHEDRON LETTERS, 1987, 28 (21) :2353-2354
[4]   SYNTHESIS OF POTENTIAL BETA-TURN BICYCLIC DIPEPTIDE MIMETICS [J].
BALDWIN, JE ;
HULME, C ;
SCHOFIELD, CJ ;
EDWARDS, AJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (11) :935-936
[5]   NOVEL CONVERSION OF AROMATIC ESTER GROUPS TO METHYL - CATALYTIC EFFECT OF IODINE IN REACTIONS INVOLVING IODOTRIMETHYLSILANE [J].
BENKESER, RA ;
MOZDZEN, EC ;
MUTH, CL .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (13) :2185-2188
[6]   Aza-annulation as a versatile approach to the synthesis of non-benzodiazepene compounds for the treatment of sleep disorders [J].
Benovsky, P ;
Stille, JR .
TETRAHEDRON LETTERS, 1997, 38 (49) :8475-8478
[7]   SYNTHESIS OF BICYCLIC PYRIDONE AND DIHYDROPYRIDONE ANALOGS OF BETA-LACTAM ANTIBIOTICS [J].
CAPPS, NK ;
DAVIES, GM ;
LOAKES, D ;
MCCABE, RW ;
YOUNG, DW .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (12) :3077-3086
[8]   LACTIM ETHER CHEMISTRY - CYCLIC BETA-ENAMINO ESTER SYNTHESIS [J].
CELERIER, JP ;
DELOISY, E ;
LHOMMET, G ;
MAITTE, P .
JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (17) :3089-3089
[9]   Synthesis and analysis of Leu-enkephalin analogues containing reverse turn peptidomimetics [J].
Claridge, TDW ;
Hulme, C ;
Kelly, RJ ;
Lee, V ;
Nash, IA ;
Schofield, CJ .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (04) :485-490
[10]   CONFORMATIONALLY CONSTRAINED DIPEPTIDES - SYNTHESIS OF 7,5-FUSED AND 6,5-FUSED BICYCLIC LACTAMS BY STEREOSELECTIVE RADICAL CYCLIZATIONS [J].
COLOMBO, L ;
DIGIACOMO, M ;
SCOLASTICO, C ;
MANZONI, L ;
BELVISI, L ;
MOLTENI, V .
TETRAHEDRON LETTERS, 1995, 36 (04) :625-628