Efficient coupling and solid-phase synthesis of steroidal ketone derivative using polymer-bound glycerol

被引：15

作者：

Maltais, R ^{[1
]}

Bérubé, M ^{[1
]}

Marion, O ^{[1
]}

Labrecque, R ^{[1
]}

Poirier, D ^{[1
]}

机构：

[1] Univ Laval, Med Res Ctr, Mol Endocrinol Lab, Div Med Chem, Quebec City, PQ G1V 4G2, Canada

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 11期

基金：

英国医学研究理事会;

关键词：

solid-phase synthesis; acetals; steroids; ketones;

D O I：

10.1016/S0040-4039(00)00050-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

High-yield coupling of steroidal hindered ketones onto polymer-bound glycerol by an efficient acetal exchange reaction is reported under mild conditions. A solid-phase model sequence of five steps is thereafter achieved to synthesize a steroidal ketone derivative having two levels of diversity in good yield and purity. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：1691 / 1694

页数：4

共 16 条

[1] A FAST PROCEDURE FOR THE REDUCTION OF AZIDES AND NITRO-COMPOUNDS BASED ON THE REDUCING ABILITY OF SN(SR)3-SPECIES [J].

BARTRA, M ;

ROMEA, P ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON, 1990, 46 (02) :587-594

[2] Potent inhibition of steroid sulfatase activity by 3-O-sulfamate 17α-benzyl(or 4′-tert-butylbenzyl)estra-1,3,5(10)-trienes:: Combination of two substituents at positions C3 and C17α of estradiol [J].

Ciobanu, LC ;

Boivin, RP ;

Luu-The, V ;

Labrie, F ;

Poirier, D .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (12) :2280-2286

[3] PREPARATION OF A POLYMER-SUPPORTED DIOL AND ITS USE IN ISOLATING ALDEHYDES AND KETONES FROM MIXTURES AND AS A PROTECTING GROUP FOR ALDEHYDES AND KETONES [J].

HODGE, P ;

WATERHOUSE, J .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1983, (10) :2319-2323

[4]

Ishihara K, 1996, SYNLETT, P839

[5] USE OF POLYMER SUPPORTS IN ORGANIC-SYNTHESIS .7. POLYMER-BOUND 1,3-DIOLS AS MONO-BLOCKING AGENTS OF SYMMETRICAL DIALDEHYDES [J].

LEZNOFF, CC ;

GREENBERG, S .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1976, 54 (24) :3824-3829

[6] USE OF POLYMER SUPPORTS IN ORGANIC SYNTHESIS .3. SELECTIVE CHEMICAL REACTIONS ON ONE ALDEHYDE GROUP OF SYMMETRICAL DIALDEHYDES [J].

LEZNOFF, CC ;

WONG, JY .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1973, 51 (22) :3756-3764

[7] Improved procedure for routine 13C NMR analysis of Merrifield resin bound molecules [J].

Lorgé, F ;

Wagner, A ;

Mioskowski, C .

JOURNAL OF COMBINATORIAL CHEMISTRY, 1999, 1 (01) :25-27

[8] A solution-phase combinatorial parallel synthesis of 3β-amido-3α-hydroxy-5α-androstane-17-ones [J].

Maltais, R ;

Poirier, D .

TETRAHEDRON LETTERS, 1998, 39 (24) :4151-4154

[9] POLYMER SUPPORTED ENANTIOSELECTIVE REACTIONS .2. ALPHA-METHYLATION OF CYCLOHEXANONE [J].

MCARTHUR, CR ;

WORSTER, PM ;

JIANG, JL ;

LEZNOFF, CC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1982, 60 (14) :1836-1841

[10] Overview of a rational approach to design type I 17β-hydroxysteroid dehydrogenase inhibitors without estrogenic activity:: Chemical synthesis and biological evaluation [J].

Tremblay, MR ;

Poirier, D .

JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 1998, 66 (04) :179-191

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