IndiumV2, Main, Exploration, bibRecord, 000A15

Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.

Identifieur interne : 000A15 ( Main/Exploration ); précédent : 000A14; suivant : 000A16

Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.

Auteurs : RBID : pubmed:22987395

English descriptors

KwdEn :
- Cyclization, Indium (chemistry), Molecular Structure, Naphthalenes (chemical synthesis), Polyenes (chemistry), Propionates (chemical synthesis), Stereoisomerism, Terpenes (chemical synthesis), Terpenes (chemistry).
MESH :
- chemical , chemical synthesis : Naphthalenes, Propionates, Terpenes.
- chemical , chemistry : Indium, Polyenes, Terpenes.
- Cyclization, Molecular Structure, Stereoisomerism.

Abstract

Cascades: An InBr(3)-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin-alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins-polyene cyclization as the key step.

DOI: 10.1002/anie.201205981
PubMed: 22987395

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Le document en format XML

<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.</title>
<author><name sortKey="Li, Bin" uniqKey="Li B">Bin Li</name>
<affiliation wicri:level="1"><nlm:affiliation>Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore.</nlm:affiliation>
<country xml:lang="fr">Singapour</country>
<wicri:regionArea>Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616</wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Lai, Yin Chang" uniqKey="Lai Y">Yin-Chang Lai</name>
</author>
<author><name sortKey="Zhao, Yujun" uniqKey="Zhao Y">Yujun Zhao</name>
</author>
<author><name sortKey="Wong, Yiu Hang" uniqKey="Wong Y">Yiu-Hang Wong</name>
</author>
<author><name sortKey="Shen, Zhi Liang" uniqKey="Shen Z">Zhi-Liang Shen</name>
</author>
<author><name sortKey="Loh, Teck Peng" uniqKey="Loh T">Teck-Peng Loh</name>
</author>
</titleStmt>
<publicationStmt><date when="2012">2012</date>
<idno type="doi">10.1002/anie.201205981</idno>
<idno type="RBID">pubmed:22987395</idno>
<idno type="pmid">22987395</idno>
<idno type="wicri:Area/Main/Corpus">000A43</idno>
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<idno type="wicri:Area/Main/Exploration">000A15</idno>
</publicationStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Cyclization</term>
<term>Indium (chemistry)</term>
<term>Molecular Structure</term>
<term>Naphthalenes (chemical synthesis)</term>
<term>Polyenes (chemistry)</term>
<term>Propionates (chemical synthesis)</term>
<term>Stereoisomerism</term>
<term>Terpenes (chemical synthesis)</term>
<term>Terpenes (chemistry)</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Naphthalenes</term>
<term>Propionates</term>
<term>Terpenes</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Indium</term>
<term>Polyenes</term>
<term>Terpenes</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Cyclization</term>
<term>Molecular Structure</term>
<term>Stereoisomerism</term>
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<front><div type="abstract" xml:lang="en">Cascades: An InBr(3)-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin-alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins-polyene cyclization as the key step.</div>
</front>
</TEI>
<pubmed><MedlineCitation Owner="NLM" Status="MEDLINE"><PMID Version="1">22987395</PMID>
<DateCreated><Year>2012</Year>
<Month>10</Month>
<Day>10</Day>
</DateCreated>
<DateCompleted><Year>2013</Year>
<Month>05</Month>
<Day>21</Day>
</DateCompleted>
<DateRevised><Year>2013</Year>
<Month>11</Month>
<Day>21</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1521-3773</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>51</Volume>
<Issue>42</Issue>
<PubDate><Year>2012</Year>
<Month>Oct</Month>
<Day>15</Day>
</PubDate>
</JournalIssue>
<Title>Angewandte Chemie (International ed. in English)</Title>
<ISOAbbreviation>Angew. Chem. Int. Ed. Engl.</ISOAbbreviation>
</Journal>
<ArticleTitle>Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.</ArticleTitle>
<Pagination><MedlinePgn>10619-23</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1002/anie.201205981</ELocationID>
<Abstract><AbstractText>Cascades: An InBr(3)-catalyzed intermolecular polyene cyclization initiated by a Prins reaction provides a concise approach to 3-oxaterpenoid derivatives. The reaction is compatible with various aldehydes, ketones, and polyolefin-alcohol substrates. In addition, the total synthesis of (±)-moluccanic acid methyl ester was achieved in seven steps by using such a Prins-polyene cyclization as the key step.</AbstractText>
<CopyrightInformation>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</CopyrightInformation>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Li</LastName>
<ForeName>Bin</ForeName>
<Initials>B</Initials>
<Affiliation>Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore.</Affiliation>
</Author>
<Author ValidYN="Y"><LastName>Lai</LastName>
<ForeName>Yin-Chang</ForeName>
<Initials>YC</Initials>
</Author>
<Author ValidYN="Y"><LastName>Zhao</LastName>
<ForeName>Yujun</ForeName>
<Initials>Y</Initials>
</Author>
<Author ValidYN="Y"><LastName>Wong</LastName>
<ForeName>Yiu-Hang</ForeName>
<Initials>YH</Initials>
</Author>
<Author ValidYN="Y"><LastName>Shen</LastName>
<ForeName>Zhi-Liang</ForeName>
<Initials>ZL</Initials>
</Author>
<Author ValidYN="Y"><LastName>Loh</LastName>
<ForeName>Teck-Peng</ForeName>
<Initials>TP</Initials>
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<Language>eng</Language>
<PublicationTypeList><PublicationType>Journal Article</PublicationType>
<PublicationType>Research Support, Non-U.S. Gov't</PublicationType>
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<ArticleDate DateType="Electronic"><Year>2012</Year>
<Month>09</Month>
<Day>17</Day>
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</Article>
<MedlineJournalInfo><Country>Germany</Country>
<MedlineTA>Angew Chem Int Ed Engl</MedlineTA>
<NlmUniqueID>0370543</NlmUniqueID>
<ISSNLinking>1433-7851</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Naphthalenes</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Polyenes</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Propionates</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>Terpenes</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance>indium bromide</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>045A6V3VFX</RegistryNumber>
<NameOfSubstance>Indium</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName MajorTopicYN="N">Cyclization</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Indium</DescriptorName>
<QualifierName MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Molecular Structure</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Naphthalenes</DescriptorName>
<QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Polyenes</DescriptorName>
<QualifierName MajorTopicYN="N">chemistry</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Propionates</DescriptorName>
<QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Stereoisomerism</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName MajorTopicYN="N">Terpenes</DescriptorName>
<QualifierName MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName MajorTopicYN="Y">chemistry</QualifierName>
</MeshHeading>
</MeshHeadingList>
</MedlineCitation>
<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2012</Year>
<Month>7</Month>
<Day>26</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="aheadofprint"><Year>2012</Year>
<Month>9</Month>
<Day>17</Day>
</PubMedPubDate>
<PubMedPubDate PubStatus="entrez"><Year>2012</Year>
<Month>9</Month>
<Day>19</Day>
<Hour>6</Hour>
<Minute>0</Minute>
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<Month>9</Month>
<Day>19</Day>
<Hour>6</Hour>
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<PubMedPubDate PubStatus="medline"><Year>2013</Year>
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<Day>23</Day>
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<PublicationStatus>ppublish</PublicationStatus>
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Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.

Synthesis of 3-oxaterpenoids and its application in the total synthesis of (±)-moluccanic acid methyl ester.

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

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