Villeneuve-la-Rivière, France
Villeneuve-la-Rivière, France

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Dumoulin D.,University of Lille Nord de France | Dumoulin D.,Laboratoire Of Chimie Organique Physique | Dumoulin D.,French National Center for Scientific Research | Lebrun S.,University of Lille Nord de France | And 11 more authors.
European Journal of Organic Chemistry | Year: 2010

The first asymmetric synthesis of phenanthroquinolizidine alkaloid (R)-boehmeriasin A is described. Two alternative synthetic pathways to the key intermediate (RS,R)-4 were achieved through a combination of highly diastereoselective 1,2-nucleophilic addition on (-)-(S)-l-amino-2-(methoxy methyl)pyrrolidine hydrazones with a ring-closing metathesis to ensure the construction of the piperidine template. A subsequent acylation/oxidation/aldol condensation/radical cyclization sequence completed the assembly of the title (R)configured natural product. © 2010 Wiley-VCH Verlag GmbH & Co. KGaA.


Ahn G.,University of Lille Nord de France | Ahn G.,Laboratoire Of Chimie Organique Physique | Lorion M.,University of Lille Nord de France | Lorion M.,Laboratoire Of Chimie Organique Physique | And 8 more authors.
Synthesis | Year: 2011

A variety of poly and diversely substituted isoindoli-nones fused with six-membered heterocyclic moieties has been readily assembled through a sequence involving metalation of N-chloroalkylated models, subsequent interception with appropriate electrophiles and ultimate intramolecular annulation reaction. © Georg Thieme Verlag Stuttgart · New York.


Lebrun S.,University of Lille Nord de France | Lebrun S.,Laboratoire Of Chimie Organique Physique | Couture A.,University of Lille Nord de France | Couture A.,CNRS Laboratory of Catalysis and Solid State Chemistry | And 4 more authors.
Synthesis | Year: 2011

A series of diversely substituted 2H-2-benzazepine-1,3-diones were efficiently prepared from the unsaturated precursors, N-acyl-o-vinylbenzamides, through a ring-closing metathesis reaction. The parent compounds were easily obtained from the appropriate o-vinylbenzoic acids. © 2011 Georg Thieme Verlag Stuttgart New York.


Dubois M.,University of Lille Nord de France | Dubois M.,Laboratoire Of Chimie Organique Physique | Deniau E.,University of Lille Nord de France | Deniau E.,Laboratoire Of Chimie Organique Physique | And 4 more authors.
Tetrahedron | Year: 2012

A flexible route for the stereoselective synthesis of a variety of 3-aryl dihydroisoquinolones and tetrahydroisoquinolines has been developed. The key step is a diastereoselective photoinduced 6π-electrocyclic ring closure of enantiopure aromatic enehydrazides via a 1,4-remote asymmetric induction. N-N bond cleavage to release the chiral appendage from the preliminary annulated compounds and/or concomitant reduction of the lactam carbonyl group completed the synthesis of the title compounds. © 2012 Elsevier Ltd. All rights reserved.


Liberge G.,University of Lille Nord de France | Liberge G.,Laboratoire Of Chimie Organique Physique | Lebrun S.,University of Lille Nord de France | Lebrun S.,Laboratoire Of Chimie Organique Physique | And 4 more authors.
Comptes Rendus Chimie | Year: 2011

A new synthetic approach for the elaboration of diversely functionalized α-methylene-γ-butyrolactones has been developed. The first step was the preliminary construction of the lactone ring system equipped with easily manageable functionalities. As the key step, the ultimate deprotonation/ methoxymethylation/β-elimination sequence allowed installation of the exocyclic olefinic moiety and then permitted chemical transformation of the above-mentioned functionalities to complete the synthesis of the title compounds. © 2011 Académie des sciences. Published by Elsevier Masson SAS. All rights reserved.


Lebrun S.,University of Lille Nord de France | Lebrun S.,Laboratoire Of Chimie Organique Physique | Couture A.,University of Lille Nord de France | Couture A.,CNRS Laboratory of Catalysis and Solid State Chemistry | And 4 more authors.
Tetrahedron Letters | Year: 2011

A variety of diversely substituted isoindeno[1,2-c]isoquinolin-5,11-diones has been readily assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates combined with a ring-closing metathesis (RCM) reaction. Intramolecular carbocationic annulation reaction and ultimate oxidation of a latent hydroxyl functionality completed the synthesis of the target titled compounds. © 2011 Elsevier Ltd. All rights reserved.


Liberge G.,University of Lille Nord de France | Liberge G.,Laboratoire Of Chimie Organique Physique | Lebrun S.,University of Lille Nord de France | Lebrun S.,Laboratoire Of Chimie Organique Physique | And 4 more authors.
Helvetica Chimica Acta | Year: 2011

A concise synthetic approach to functionalized α- methylidenebutanolactams has been developed. The synthetic strategy is based on the preliminary assembly of the lactam template equipped with appropriate functionalities. Subsequent installation of the methylidene by a metalation/alkylation/elimination sequence completed the elaboration of the racemic title compounds. Copyright © 2011 Verlag Helvetica Chimica Acta AG, Zürich, Switzerland.


Agouridas V.,University of Lille Nord de France | Agouridas V.,Laboratoire Of Chimie Organique Physique | Capet F.,University of Lille Nord de France | Capet F.,CNRS Laboratory of Catalysis and Solid State Chemistry | And 6 more authors.
Tetrahedron Asymmetry | Year: 2011

A new methodology for the asymmetric synthesis of C-3 alkylated isoindolinones has been developed through a novel extension of Meyers' lactamisation. The key polycyclic lactam precursor was prepared in high yield and high diastereoselectivity by a two step sequence involving phthalic anhydride and aminoprolinol. Metallation/alkylation followed by hydride reduction of the transient N-acylhydrazonium species and ultimate removal of the chiral auxiliary without a loss of stereochemical integrity completed the synthesis of the target compounds. © 2011 Elsevier Ltd. All rights reserved.


Lorion M.,University of Lille Nord de France | Lorion M.,Laboratoire Of Chimie Organique Physique | Agouridas V.,University of Lille Nord de France | Agouridas V.,Laboratoire Of Chimie Organique Physique | And 6 more authors.
Tetrahedron Letters | Year: 2010

A series of cis-locked stilbenic compounds related to combretastatin and combretastatin A4 has been designed and synthesized. The cytotoxic effects of these rigid analogues were evaluated as well as their abilities to inhibit tubulin polymerization. © 2010 Elsevier Ltd. All rights reserved.


Lebrun S.,University of Lille Nord de France | Lebrun S.,Laboratoire Of Chimie Organique Physique | Couture A.,University of Lille Nord de France | Couture A.,CNRS Laboratory of Catalysis and Solid State Chemistry | And 4 more authors.
Synthesis | Year: 2012

A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor. © Georg Thieme Verlag Stuttgart · New York.

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