Stereoselective Synthesis of Fluorinated 1,3-cis-Diaminocyclopentanes

被引：14

作者：

Pasco, Morgane ^{[1
]}

Moumne, Roba ^{[1
]}

Lecourt, Thomas ^{[1
]}

Micouin, Laurent ^{[1
]}

机构：

[1] Paris Descartes Univ, Lab Chim Therapeut, Fac Sci Pharmaceut & Biol, CNRS,UMR8638, F-75006 Paris, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 12期

关键词：

FRAGMENT-BASED APPROACH; XENON DIFLUORIDE; LIGANDS; DESIGN; OLEFINS;

D O I：

10.1021/jo2001512

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Several fluorinated 1,3-diaminocyclopentanes, previously reported to be useful RNA structural probes, can be prepared in a diastereoselective manner from a single bicyclic hydrazine precursor, in 3 to 9 steps.

引用

页码：5137 / 5142

页数：6

共 18 条

[1]

Begis G., 2006, Patent application WO, Patent No. 2006024784

[2] FLUORO CARBOCYCLIC NUCLEOSIDES - SYNTHESIS AND ANTIVIRAL ACTIVITY OF 2'-FLUORO AND 6'-FLUORO CARBOCYCLIC PYRIMIDINE NUCLEOSIDES INCLUDING CARBOCYCLIC 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-METHYLURACIL AND CARBOCYCLIC 1-(2-DEOXY-2-FLUORO-BETA-D-ARABINOFURANOSYL)-5-IODOURACIL [J].

BORTHWICK, AD ;

EVANS, DN ;

KIRK, BE ;

BIGGADIKE, K ;

EXALL, AM ;

YOUDS, P ;

ROBERTS, SM ;

KNIGHT, DJ ;

COATES, JAV .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (01) :179-186

[3] Skeletal rearrangements in the 2,3-diazanorbornene series. A fast access to highly functionalized cyclopentanes [J].

Bournaud, Chloee ;

Bonin, Martine ;

Micouin, Laurent .

ORGANIC LETTERS, 2006, 8 (14) :3041-3043

[4] NMR-Guided fragment-based approach for the design of tRNALys3 ligands [J].

Chung, Florence ;

Tisne, Carine ;

Lecourt, Thomas ;

Dardel, Frederic ;

Micouin, Laurent .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (24) :4489-4491

[5] Design of tRNA3Lys Ligands: Fragment Evolution and Linker Selection Guided by NMR Spectroscopy [J].

Chung, Florence ;

Tisne, Carine ;

Lecourt, Thomas ;

Seijo, Bili ;

Dardel, Frederic ;

Micouin, Laurent .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (29) :7109-7116

[6] Ligand- and substrate-based 19F NMR screening:: Principles and applications to drug discovery [J].

Dalvit, Claudio .

PROGRESS IN NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY, 2007, 51 (04) :243-I

[7] NMR-guided fragment-based approach for the design of AAC(6′)-Ib ligands [J].

Lombes, Thomas ;

Begis, Guillaume ;

Maurice, Frederique ;

Turcaud, Serge ;

Lecourt, Thomas ;

Dardel, Frederic ;

Micouin, Laurent .

CHEMBIOCHEM, 2008, 9 (09) :1368-1371

[8] Enantio selective desymmetrization of meso bicyclic hydrazines: A novel approach to the asymmetric synthesis of polysubstituted amino cyclopentanic cores [J].

Luna, AP ;

Ceschi, MA ;

Bonin, M ;

Micouin, L ;

Husson, HP ;

Gougeon, S ;

Estenne-Bouhtou, G ;

Marabout, B ;

Sevrin, M ;

George, P .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10) :3522-3524

[9] Rearrangement of β-amino alcohols via aziridiniums: a review [J].

Metro, Thomas-Xavier ;

Duthion, Beranger ;

Pardo, Domingo Gomez ;

Cossy, Janine .

CHEMICAL SOCIETY REVIEWS, 2010, 39 (01) :89-102

[10] Predicting properties and tuning physicochemical in lead optimization:: Amine basicities [J].

Morgenthaler, Martin ;

Schweizer, Eliane ;

Hoffmann-Roeder, Ania ;

Benini, Fausta ;

Martin, Rainer E. ;

Jaeschke, Georg ;

Wagner, Bjoern ;

Fischer, Holger ;

Bendels, Stefanie ;

Zimmerli, Daniel ;

Schneider, Josef ;

Diederich, Francois ;

Kansy, Manfred ;

Mueller, Klaus .

CHEMMEDCHEM, 2007, 2 (08) :1100-1115

← 1 2 →