Publikation:

Enantioselective Total Synthesis of (+)-Pepluanol A

Vorschaubild

Dateien

Zu diesem Dokument gibt es keine Dateien.

Datum

2022

Autor:innen

Herausgeber:innen

Kontakt

ISSN der Zeitschrift

Electronic ISSN

ISBN

Bibliografische Daten

Verlag

Schriftenreihe

Auflagebezeichnung

URI (zitierfähiger Link)
DOI (zitierfähiger Link)
https://doi.org/10.1021/acs.orglett.2c00961
ArXiv-ID

Internationale Patentnummer

Angaben zur Forschungsförderung

Projekt

Open Access-Veröffentlichung

Sammlungen

Chemie: Publikationen
Core Facility der Universität Konstanz

Gesperrt bis

Titel in einer weiteren Sprache

Publikationstyp
Zeitschriftenartikel
Publikationsstatus
Published

Erschienen in

Organic letters. American Chemical Society (ACS). 2022, 24, pp. 4717-4721. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.2c00961

Zusammenfassung

Herein, we report an enantioselective and convergent total synthesis of (+)-pepluanol A, a structurally intriguing Euphorbia diterpenoid natural product featuring a 5/6/7/3-fused tetracyclic skeleton, from known building blocks in 11 steps. The successful strategy relies on a phenyl selenide-mediated Morita-Baylis-Hillman type reaction as a connective step, forging the precursor for the key intramolecular Diels-Alder reaction to construct the congested 5/6/7-tricyclic framework. A diastereoconvergent cascade starting with an acid-induced removal of the C1-MOM protecting group followed by a retro-aldol/aldol reaction resulted in the formation of a single diastereomer. This stereoconvergency allowed for the successful substrate-controlled diastereoselective cyclopropanation of an advanced intermediate to establish the full carboskeleton of (+)-pepluanol A (1).

Zusammenfassung in einer weiteren Sprache

Fachgebiet (DDC)
540 Chemie

Schlagwörter

Konferenz

Rezension
undefined / . - undefined, undefined

Forschungsvorhaben

Organisationseinheiten

Zeitschriftenheft

Zugehörige Datensätze in KOPS

Zitieren

ISO 690YUAN, Po, Tanja GAICH, 2022. Enantioselective Total Synthesis of (+)-Pepluanol A. In: Organic letters. American Chemical Society (ACS). 2022, 24, pp. 4717-4721. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.2c00961
BibTex
@article{Yuan2022Enant-58032,
  year={2022},
  doi={10.1021/acs.orglett.2c00961},
  title={Enantioselective Total Synthesis of (+)-Pepluanol A},
  volume={24},
  issn={1523-7060},
  journal={Organic letters},
  pages={4717--4721},
  author={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/123456789/58032">
    <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/58032"/>
    <dcterms:abstract xml:lang="eng">Herein, we report an enantioselective and convergent total synthesis of (+)-pepluanol A, a structurally intriguing Euphorbia diterpenoid natural product featuring a 5/6/7/3-fused tetracyclic skeleton, from known building blocks in 11 steps. The successful strategy relies on a phenyl selenide-mediated Morita-Baylis-Hillman type reaction as a connective step, forging the precursor for the key intramolecular Diels-Alder reaction to construct the congested 5/6/7-tricyclic framework. A diastereoconvergent cascade starting with an acid-induced removal of the C1-MOM protecting group followed by a retro-aldol/aldol reaction resulted in the formation of a single diastereomer. This stereoconvergency allowed for the successful substrate-controlled diastereoselective cyclopropanation of an advanced intermediate to establish the full carboskeleton of (+)-pepluanol A (1).</dcterms:abstract>
    <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dc:creator>Gaich, Tanja</dc:creator>
    <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/server/rdf/resource/123456789/29"/>
    <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-07-13T14:09:21Z</dcterms:available>
    <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/>
    <dc:creator>Yuan, Po</dc:creator>
    <dcterms:issued>2022</dcterms:issued>
    <dc:contributor>Yuan, Po</dc:contributor>
    <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-07-13T14:09:21Z</dc:date>
    <dc:contributor>Gaich, Tanja</dc:contributor>
    <dc:language>eng</dc:language>
    <foaf:homepage rdf:resource="http://localhost:8080/"/>
    <dcterms:title>Enantioselective Total Synthesis of (+)-Pepluanol A</dcterms:title>
  </rdf:Description>
</rdf:RDF>

Interner Vermerk

xmlui.Submission.submit.DescribeStep.inputForms.label.kops_note_fromSubmitter

Kontakt
URL der Originalveröffentl.

Prüfdatum der URL

Prüfungsdatum der Dissertation

Finanzierungsart

Kommentar zur Publikation

Allianzlizenz
Corresponding Authors der Uni Konstanz vorhanden
Internationale Co-Autor:innen
Universitätsbibliographie
Ja
Begutachtet
Ja
Diese Publikation teilen