New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.
Identifieur interne : 000255 ( PubMed/Curation ); précédent : 000254; suivant : 000256New 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
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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><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">18549283</PMID><DateCreated><Year>2008</Year><Month>7</Month><Day>11</Day></DateCreated><DateCompleted><Year>2008</Year><Month>09</Month><Day>26</Day></DateCompleted><DateRevised><Year>2008</Year><Month>7</Month><Day>11</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-6904</ISSN><JournalIssue CitedMedium="Internet"><Volume>73</Volume><Issue>14</Issue><PubDate><Year>2008</Year><Month>Jul</Month><Day>18</Day></PubDate></JournalIssue><Title>The Journal of organic chemistry</Title><ISOAbbreviation>J. Org. Chem.</ISOAbbreviation></Journal><ArticleTitle>New and expeditious tandem sequence aza-Michael/intramolecular nucleophilic substitution route to substituted gamma-lactams: synthesis of the tricyclic core of (+/-)-martinellines.</ArticleTitle><Pagination><MedlinePgn>5566-9</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/jo702752w</ELocationID><Abstract><AbstractText>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.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Comesse</LastName><ForeName>Sébastien</ForeName><Initials>S</Initials><AffiliationInfo><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</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Sanselme</LastName><ForeName>Morgane</ForeName><Initials>M</Initials></Author><Author ValidYN="Y"><LastName>Daïch</LastName><ForeName>Adam</ForeName><Initials>A</Initials></Author></AuthorList><Language>ENG</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2008</Year><Month>Jun</Month><Day>13</Day></ArticleDate></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Org Chem</MedlineTA><NlmUniqueID>2985193R</NlmUniqueID><ISSNLinking>0022-3263</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D001372">Aza Compounds</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007769">Lactams</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011758">Pyrroles</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011804">Quinolines</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="C410408">martinelline</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D001372" MajorTopicYN="N">Aza Compounds</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007769" MajorTopicYN="N">Lactams</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D015394" MajorTopicYN="N">Molecular Structure</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011758" MajorTopicYN="N">Pyrroles</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011804" MajorTopicYN="N">Quinolines</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013237" MajorTopicYN="N">Stereoisomerism</DescriptorName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2008</Year><Month>6</Month><Day>14</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2008</Year><Month>9</Month><Day>27</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2008</Year><Month>6</Month><Day>14</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">18549283</ArticleId><ArticleId IdType="doi">10.1021/jo702752w</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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