Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues

被引:33
作者
Fadel, A
GarciaArgote, S
机构
[1] Laboratoire des Carbocycles, Inst. de Chimie Moleculaire d'Orsay, Universite de Paris-Sud
关键词
D O I
10.1016/0957-4166(96)00122-X
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
From a single chiron (R)-(+)-5, available with high enantiomeric excess (97%) by enzymatic hydrolysis (PLE acetonic powder) of a malonate, were prepared convenient precursors of aminoglutethimides (-)-AG-1 and (+)-AG-1. This versatile method also allows preparation of the b-hydroxy ester (R)-9 and its enantiomer (S)-9 as well as the glutethimides (S)-4 and (R)-4 and other analogues. Copyright (C) 1996 Elsevier Science Ltd
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页码:1159 / 1166
页数:8
相关论文
共 24 条
[1]   HORNER-WADSWORTH-EMMONS REACTION - USE OF LITHIUM-CHLORIDE AND AN AMINE FOR BASE SENSITIVE COMPOUNDS [J].
BLANCHETTE, MA ;
CHOY, W ;
DAVIS, JT ;
ESSENFELD, AP ;
MASAMUNE, S ;
ROUSH, WR ;
SAKAI, T .
TETRAHEDRON LETTERS, 1984, 25 (21) :2183-2186
[2]  
CANET JL, 1992, J ORG CHEM, V57, P346
[3]   SYNTHESIS AND BIOCHEMICAL EVALUATION OF ANALOGS OF AMINOGLUTETHIMIDE BASED ON PHENYLPYRROLIDINE-2,5-DIONE [J].
DALY, MJ ;
JONES, GW ;
NICHOLLS, PJ ;
SMITH, HJ ;
ROWLANDS, MG .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (04) :520-523
[4]   ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - TOTAL SYNTHESES OF (+)-EPILAURENE AND (-)-ISOLAURENE [J].
FADEL, A ;
CANET, JL ;
SALAUN, J .
TETRAHEDRON-ASYMMETRY, 1993, 4 (01) :27-30
[5]   ASYMMETRIC CONSTRUCTION OF BENZYLIC QUATERNARY CARBONS FROM CHIRAL MALONATES - FORMAL SYNTHESIS OF NATURAL (-)APHANORPHINE [J].
FADEL, A ;
ARZEL, P .
TETRAHEDRON-ASYMMETRY, 1995, 6 (04) :893-900
[6]   BAKERS YEAST-MEDIATED SYNTHESIS OF (R)-AMINOGLUTETHIMIDE [J].
FOGLIATO, G ;
FRONZA, G ;
FUGANTI, C ;
GRASSELLI, P ;
SERVI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (17) :5693-5695
[7]   ANALOGS OF AMINOGLUTETHIMIDE - SELECTIVE-INHIBITION OF CHOLESTEROL SIDE-CHAIN CLEAVAGE [J].
FOSTER, AB ;
JARMAN, M ;
LEUNG, CS ;
ROWLANDS, MG ;
TAYLOR, GN .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (01) :50-54
[8]   SYNTHESIS AND AROMATASE INHIBITION OF 3-CYCLOALKYL-SUBSTITUTED 3-(4-AMINOPHENYL)PIPERIDINE-2,6-DIONES [J].
HARTMANN, RW ;
BATZL, C ;
PONGRATZ, TM ;
MANNSCHRECK, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (12) :2210-2214
[9]  
HARVEY HA, 1982, CANCER RES S, V42, pS3261
[10]  
Hoffmann K., 1958, U.S. Patent, Patent No. [2,848,455, 2848455]