LeHavreV1, Main, Exploration, bibRecord, 000456

Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.

Identifieur interne : 000456 ( Main/Exploration ); précédent : 000455; suivant : 000457

Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.

Auteurs : Ronan Le Goff [France] ; Ata Martin Lawson ; Adam Daïch ; Sébastien Comesse

Source :

Organic & biomolecular chemistry [ 1477-0539 ] ; 2013.

RBID : pubmed:23400342

English descriptors

KwdEn :
- Aniline Compounds (chemical synthesis), Aniline Compounds (chemistry), Molecular Structure, Pyrroles (chemical synthesis), Pyrroles (chemistry), Pyrrolidines (chemical synthesis), Pyrrolidines (chemistry), Quinolines (chemical synthesis), Quinolines (chemistry), Stereoisomerism.
MESH :
- chemical , chemical synthesis : Aniline Compounds, Pyrroles, Pyrrolidines, Quinolines.
- chemical , chemistry : Aniline Compounds, Pyrroles, Pyrrolidines, Quinolines.
- Molecular Structure, Stereoisomerism.

Abstract

An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl)carbamate with various Michael acceptors is described. The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.

DOI: 10.1039/c3ob27472a
PubMed: 23400342

Affiliations:

Le document en format XML

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<affiliation wicri:level="4"><nlm:affiliation>URCOM, EA 3221, INC3M, FR-CNRS 3038, UFR des Sciences & Techniques de l'Université du Havre, BP: 540, 25 rue Philippe Lebon, F-76058 Le Havre Cedex, France.</nlm:affiliation>
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<author><name sortKey="Lawson, Ata Martin" sort="Lawson, Ata Martin" uniqKey="Lawson A" first="Ata Martin" last="Lawson">Ata Martin Lawson</name>
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<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
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<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
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<author><name sortKey="Lawson, Ata Martin" sort="Lawson, Ata Martin" uniqKey="Lawson A" first="Ata Martin" last="Lawson">Ata Martin Lawson</name>
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<series><title level="j">Organic & biomolecular chemistry</title>
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<term>Pyrroles (chemistry)</term>
<term>Pyrrolidines (chemical synthesis)</term>
<term>Pyrrolidines (chemistry)</term>
<term>Quinolines (chemical synthesis)</term>
<term>Quinolines (chemistry)</term>
<term>Stereoisomerism</term>
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<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Aniline Compounds</term>
<term>Pyrroles</term>
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<term>Quinolines</term>
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<front><div type="abstract" xml:lang="en">An aza-Michael induced ring closure (aza-MIRC) tandem reaction of benzyl (2-bromoethyl)carbamate with various Michael acceptors is described. The N-Cbz-β-gem-disubstituted pyrrolidines thus obtained were proved to be versatile intermediates for the rapid access to both martinelline and spirooxindole backbones. An application of this strategy towards an expedient 4 step total synthesis of (±)-coerulescine is also presented.</div>
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<name sortKey="Lawson, Ata Martin" sort="Lawson, Ata Martin" uniqKey="Lawson A" first="Ata Martin" last="Lawson">Ata Martin Lawson</name>
</noCountry>
<country name="France"><region name="Région Normandie"><name sortKey="Le Goff, Ronan" sort="Le Goff, Ronan" uniqKey="Le Goff R" first="Ronan" last="Le Goff">Ronan Le Goff</name>
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</record>

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Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.

Synthesis of highly functionalized pyrrolidines as tunable templates for the direct access to (±)-coerulescine and the tricyclic core of martinellines.

Source :

English descriptors

Abstract

Links toward previous steps (curation, corpus...)

Le document en format XML

Pour manipuler ce document sous Unix (Dilib)

Pour mettre un lien sur cette page dans le réseau Wicri

Pour générer des pages wiki

	Serveur d'exploration sur la visibilité du Havre
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