An efficient synthesis of N-benzyl-3-sulfonyl glutarimides.: Formal synthesis of the aromatase inhibitor AG-1

被引:37
作者
Chang, MY [1 ]
Chang, BR [1 ]
Tai, HM [1 ]
Chang, NC [1 ]
机构
[1] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan
关键词
D O I
10.1016/S0040-4039(00)01845-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A formal [3+3] cycloaddition strategy to substituted glutarimides was studied. N-Benzyl alpha -sulfonyl-acetamides and various alpha,beta -unsaturated esters were used as starting materials. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:10273 / 10276
页数:4
相关论文
共 17 条
[1]   Resolution of 4 cyano-4-(4-nitrophenyl)hexanoic acid: Synthesis of (R) and (S)-3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione (aminoglutethimide) [J].
Achmatowicz, O ;
Malinowska, I ;
Szechner, B ;
Maurin, JK .
TETRAHEDRON, 1997, 53 (23) :7917-7928
[2]   The synthesis of (±)-aminoglutethimide via vicarious nucleophilic aromatic substitution of hydrogen [J].
Bushell, SM ;
Crump, JP ;
Lawrence, NJ ;
Pineau, G .
TETRAHEDRON, 1998, 54 (10) :2269-2274
[3]  
Dawson N, 1998, CLIN CANCER RES, V4, P37
[4]   Asymmetric construction of benzylic quaternary carbons from chiral malonates: Formal synthesis of both (-)- and (+)-aminoglutethimides AG and analogues [J].
Fadel, A ;
GarciaArgote, S .
TETRAHEDRON-ASYMMETRY, 1996, 7 (04) :1159-1166
[5]   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
[6]   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
[7]  
HARVEY HA, 1982, CANCER RES S, V42, pS3261
[8]   BOP AS A REAGENT FOR MILD AND EFFICIENT PREPARATION OF ESTERS [J].
KIM, MH ;
PATEL, DV .
TETRAHEDRON LETTERS, 1994, 35 (31) :5603-5606
[9]  
KNABE J, 1987, ARCH PHARM, V330, P1032
[10]   ANALOGS OF 3-ETHYL-3-(4-PYRIDYL)PIPERIDINE-2,6-DIONE AS SELECTIVE INHIBITORS OF AROMATASE - DERIVATIVES WITH VARIABLE 1-ALKYL AND 3-ALKYL SUBSTITUENTS [J].
LEUNG, CS ;
ROWLANDS, MG ;
JARMAN, M ;
FOSTER, AB ;
GRIGGS, LJ ;
WILMAN, DEV .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) :1550-1554