An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5
An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5
Date
2020
Editors
Journal ISSN
Electronic ISSN
ISBN
Bibliographical data
Publisher
Series
URI (citable link)
DOI (citable link)
International patent number
Link to the license
EU project number
Project
Open Access publication
Collections
Title in another language
Publication type
Journal article
Publication status
Published
Published in
Angewandte Chemie International Edition ; 59 (2020), 14. - pp. 5521-5525. - Wiley. - ISSN 1433-7851. - eISSN 1521-3773
Abstract
We report a concise and versatile total synthesis of the diterpenoid (+)-norcembrene 5 from simple building blocks. A ring-closing metathesis as well as an auxiliary-directed 1,4-addition represent the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structure motif was established from a furanocembranoid via transannular [4+2] cycloaddition.
Summary in another language
Subject (DDC)
540 Chemistry
Keywords
furanocembranoid, norcembrenolide, ring-closing metathesis, total synthesis, transannular [4+2] cycloaddition
Conference
Review
undefined / . - undefined, undefined. - (undefined; undefined)
Cite This
ISO 690
BREUNIG, Michael, Po YUAN, Tanja GAICH, 2020. An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5. In: Angewandte Chemie International Edition. Wiley. 59(14), pp. 5521-5525. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.201912613BibTex
@article{Breunig2020Unexp-47761, year={2020}, doi={10.1002/anie.201912613}, title={An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5}, number={14}, volume={59}, issn={1433-7851}, journal={Angewandte Chemie International Edition}, pages={5521--5525}, author={Breunig, Michael and Yuan, Po and Gaich, Tanja} }
RDF
<rdf:RDF xmlns:dcterms="http://purl.org/dc/terms/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dspace="http://digital-repositories.org/ontologies/dspace/0.1.0#" xmlns:foaf="http://xmlns.com/foaf/0.1/" xmlns:void="http://rdfs.org/ns/void#" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/server/rdf/resource/123456789/47761"> <dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/47761/1/Breunig_2-1qxvx0tkqtvzn1.pdf"/> <dcterms:abstract xml:lang="eng">We report a concise and versatile total synthesis of the diterpenoid (+)-norcembrene 5 from simple building blocks. A ring-closing metathesis as well as an auxiliary-directed 1,4-addition represent the key steps of our synthetic route. During the synthesis, an unprecedented, highly oxidized pentacyclic structure motif was established from a furanocembranoid via transannular [4+2] cycloaddition.</dcterms:abstract> <dc:rights>Attribution-NonCommercial-NoDerivatives 4.0 International</dc:rights> <dc:contributor>Gaich, Tanja</dc:contributor> <dcterms:issued>2020</dcterms:issued> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-12-02T10:50:34Z</dcterms:available> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/> <dc:creator>Yuan, Po</dc:creator> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2019-12-02T10:50:34Z</dc:date> <dc:contributor>Breunig, Michael</dc:contributor> <dcterms:rights rdf:resource="http://creativecommons.org/licenses/by-nc-nd/4.0/"/> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dc:contributor>Yuan, Po</dc:contributor> <foaf:homepage rdf:resource="http://localhost:8080/"/> <dc:creator>Breunig, Michael</dc:creator> <dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/47761/1/Breunig_2-1qxvx0tkqtvzn1.pdf"/> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/> <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/47761"/> <dcterms:title>An Unexpected Transannular [4+2] Cycloaddition during the Total Synthesis of (+)-Norcembrene 5</dcterms:title> <dc:creator>Gaich, Tanja</dc:creator> <dc:language>eng</dc:language> </rdf:Description> </rdf:RDF>
Internal note
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Examination date of dissertation
Method of financing
Comment on publication
Alliance license
Corresponding Authors der Uni Konstanz vorhanden
International Co-Authors
Bibliography of Konstanz
Yes
Refereed
Yes