New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Identifieur interne : 000A24 ( France/Analysis ); précédent : 000A23; suivant : 000A25New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Auteurs : Sébastien Comesse [France] ; Morgane Sanselme ; Adam DaïchSource :
- The Journal of organic chemistry [ 1520-6904 ] ; 2008.
English descriptors
- KwdEn :
- MESH :
- chemical , chemical synthesis : Pyrroles, Quinolines.
- chemical , chemistry : Aza Compounds, Lactams, Pyrroles, Quinolines.
- Molecular Structure, Stereoisomerism.
Abstract
A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of (+/-)-martinelline alkaloids is also described.
DOI: 10.1021/jo702752w
PubMed: 18549283
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: 000255
- to stream PubMed, to step Curation: 000255
- to stream PubMed, to step Checkpoint: 000255
- to stream Ncbi, to step Merge: 000211
- to stream Ncbi, to step Curation: 000211
- to stream Ncbi, to step Checkpoint: 000211
- to stream Main, to step Merge: 000D59
- to stream Main, to step Curation: 000D48
- to stream Main, to step Exploration: 000D48
- to stream France, to step Extraction: 000A24
Links to Exploration step
pubmed:18549283Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.</title>
<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<affiliation wicri:level="4"><nlm:affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex, France. sebastien.comesse@univ-lehavre.fr</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
<orgName type="university">Université du Havre</orgName>
</affiliation>
</author>
<author><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name>
</author>
<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
</author>
</titleStmt>
<publicationStmt><idno type="wicri:source">PubMed</idno>
<date when="2008">2008</date>
<idno type="RBID">pubmed:18549283</idno>
<idno type="pmid">18549283</idno>
<idno type="doi">10.1021/jo702752w</idno>
<idno type="wicri:Area/PubMed/Corpus">000255</idno>
<idno type="wicri:Area/PubMed/Curation">000255</idno>
<idno type="wicri:Area/PubMed/Checkpoint">000255</idno>
<idno type="wicri:Area/Ncbi/Merge">000211</idno>
<idno type="wicri:Area/Ncbi/Curation">000211</idno>
<idno type="wicri:Area/Ncbi/Checkpoint">000211</idno>
<idno type="wicri:Area/Main/Merge">000D59</idno>
<idno type="wicri:Area/Main/Curation">000D48</idno>
<idno type="wicri:Area/Main/Exploration">000D48</idno>
<idno type="wicri:Area/France/Extraction">000A24</idno>
</publicationStmt>
<sourceDesc><biblStruct><analytic><title xml:lang="en">New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.</title>
<author><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
<affiliation wicri:level="4"><nlm:affiliation>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex, France. sebastien.comesse@univ-lehavre.fr</nlm:affiliation>
<country xml:lang="fr">France</country>
<wicri:regionArea>URCOM, EA 3221, UFR des Sciences & Techniques, Université du Havre, 25 rue Philippe Lebon, BP 540, F-76058 Le Havre Cedex</wicri:regionArea>
<placeName><region type="region" nuts="2">Région Normandie</region>
<region type="old region" nuts="2">Haute-Normandie</region>
<settlement type="city">Le Havre</settlement>
</placeName>
<orgName type="university">Université du Havre</orgName>
</affiliation>
</author>
<author><name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name>
</author>
<author><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
</author>
</analytic>
<series><title level="j">The Journal of organic chemistry</title>
<idno type="eISSN">1520-6904</idno>
<imprint><date when="2008" type="published">2008</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aza Compounds (chemistry)</term>
<term>Lactams (chemistry)</term>
<term>Molecular Structure</term>
<term>Pyrroles (chemical synthesis)</term>
<term>Pyrroles (chemistry)</term>
<term>Quinolines (chemical synthesis)</term>
<term>Quinolines (chemistry)</term>
<term>Stereoisomerism</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Pyrroles</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Aza Compounds</term>
<term>Lactams</term>
<term>Pyrroles</term>
<term>Quinolines</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Molecular Structure</term>
<term>Stereoisomerism</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A new and highly diastereoselective tandem reaction aza-Michael/intramolecular nucleophilic substitution is presented. This unprecedented tandem reaction between N-substituted alpha-bromoacetamides and Michael acceptors proceeds with good yields and excellent diastereoselectivity to provide the corresponding trisubstituted gamma-lactam systems. An application to the concise synthesis of the tricyclic core of (+/-)-martinelline alkaloids is also described.</div>
</front>
</TEI>
<affiliations><list><country><li>France</li>
</country>
<region><li>Haute-Normandie</li>
<li>Région Normandie</li>
</region>
<settlement><li>Le Havre</li>
</settlement>
<orgName><li>Université du Havre</li>
</orgName>
</list>
<tree><noCountry><name sortKey="Daich, Adam" sort="Daich, Adam" uniqKey="Daich A" first="Adam" last="Daïch">Adam Daïch</name>
<name sortKey="Sanselme, Morgane" sort="Sanselme, Morgane" uniqKey="Sanselme M" first="Morgane" last="Sanselme">Morgane Sanselme</name>
</noCountry>
<country name="France"><region name="Région Normandie"><name sortKey="Comesse, Sebastien" sort="Comesse, Sebastien" uniqKey="Comesse S" first="Sébastien" last="Comesse">Sébastien Comesse</name>
</region>
</country>
</tree>
</affiliations>
</record>
Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Wicri/France/explor/LeHavreV1/Data/France/Analysis
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000A24 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/France/Analysis/biblio.hfd -nk 000A24 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien |wiki= Wicri/France |area= LeHavreV1 |flux= France |étape= Analysis |type= RBID |clé= pubmed:18549283 |texte= New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines. }}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/France/Analysis/RBID.i -Sk "pubmed:18549283" \ | HfdSelect -Kh $EXPLOR_AREA/Data/France/Analysis/biblio.hfd \ | NlmPubMed2Wicri -a LeHavreV1
This area was generated with Dilib version V0.6.25. |