Publikation: Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate
Lade...
Dateien
Datum
2017
Autor:innen
Dickschat, Jeroen S.
Herausgeber:innen
ISSN der Zeitschrift
Electronic ISSN
ISBN
Bibliografische Daten
Verlag
Schriftenreihe
Auflagebezeichnung
URI (zitierfähiger Link)
DOI (zitierfähiger Link)
Internationale Patentnummer
Link zur Lizenz
Angaben zur Forschungsförderung
Projekt
Open Access-Veröffentlichung
Open Access Green
Sammlungen
Core Facility der Universität Konstanz
Titel in einer weiteren Sprache
Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published
Erschienen in
European Journal of Organic Chemistry. Wiley-Blackwell - STM. 2017(31), pp. 4566-4571. ISSN 1434-2421. eISSN 1099-0682. Available under: doi: 10.1002/ejoc.201700882
Zusammenfassung
The asymmetric synthesis of both enantiomers of tetrasubstituted all-trans dimethyl 3,4-diacetylcyclobutane-1,2-dicarboxylate with high enantiomeric purity (>98 % ee) using a valine-derived chiral auxiliary in a diastereoselective photodimerization is reported. The absolute configuration was assigned by single-crystal X-ray diffraction analysis. Because this cyclobutane is a key intermediate in the total synthesis of (–)-sceptrin and ageliferin, our findings strengthen the recently revised absolute configurations of these pyrrole-imidazole alkaloids. An enantioselective synthesis of a tetrasubstituted all-trans cyclobutane, a key intermediate in the total synthesis of the pyrrole-imidazole alkaloid sceptrin, facilitated by a diastereoselective, valine-derived chiral-auxiliary-guided photodimerization, is reported.
Zusammenfassung in einer weiteren Sprache
Fachgebiet (DDC)
540 Chemie
Schlagwörter
Konferenz
Rezension
undefined / . - undefined, undefined
Zitieren
ISO 690
BARRA, Lena, Jeroen S. DICKSCHAT, 2017. Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate. In: European Journal of Organic Chemistry. Wiley-Blackwell - STM. 2017(31), pp. 4566-4571. ISSN 1434-2421. eISSN 1099-0682. Available under: doi: 10.1002/ejoc.201700882BibTex
@article{Barra2017Scept-57696,
year={2017},
doi={10.1002/ejoc.201700882},
title={Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate},
number={31},
issn={1434-2421},
journal={European Journal of Organic Chemistry},
pages={4566--4571},
author={Barra, Lena and Dickschat, Jeroen S.}
}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/123456789/57696">
<dc:creator>Barra, Lena</dc:creator>
<foaf:homepage rdf:resource="http://localhost:8080/"/>
<dcterms:hasPart rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/57696/1/Barra_2-mi6dzno8s8qb2.pdf"/>
<dc:creator>Dickschat, Jeroen S.</dc:creator>
<bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/57696"/>
<dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
<dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-05-30T10:29:44Z</dc:date>
<dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
<dc:contributor>Barra, Lena</dc:contributor>
<dcterms:issued>2017</dcterms:issued>
<dc:rights>terms-of-use</dc:rights>
<dc:language>eng</dc:language>
<dcterms:rights rdf:resource="https://rightsstatements.org/page/InC/1.0/"/>
<dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-05-30T10:29:44Z</dcterms:available>
<dcterms:abstract xml:lang="eng">The asymmetric synthesis of both enantiomers of tetrasubstituted all-trans dimethyl 3,4-diacetylcyclobutane-1,2-dicarboxylate with high enantiomeric purity (>98 % ee) using a valine-derived chiral auxiliary in a diastereoselective photodimerization is reported. The absolute configuration was assigned by single-crystal X-ray diffraction analysis. Because this cyclobutane is a key intermediate in the total synthesis of (–)-sceptrin and ageliferin, our findings strengthen the recently revised absolute configurations of these pyrrole-imidazole alkaloids. An enantioselective synthesis of a tetrasubstituted all-trans cyclobutane, a key intermediate in the total synthesis of the pyrrole-imidazole alkaloid sceptrin, facilitated by a diastereoselective, valine-derived chiral-auxiliary-guided photodimerization, is reported.</dcterms:abstract>
<void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
<dspace:hasBitstream rdf:resource="https://kops.uni-konstanz.de/bitstream/123456789/57696/1/Barra_2-mi6dzno8s8qb2.pdf"/>
<dc:contributor>Dickschat, Jeroen S.</dc:contributor>
<dcterms:title>Sceptrin : Enantioselective Synthesis of a Tetrasubstituted all-trans Cyclobutane Key Intermediate</dcterms:title>
</rdf:Description>
</rdf:RDF>Interner Vermerk
xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter
Prüfungsdatum der Dissertation
Finanzierungsart
Kommentar zur Publikation
Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Nein
Begutachtet
Ja
