Enantioselective Total Synthesis of (+)-Pepluanol A

Cite This

Files in this item

Files Size Format View

There are no files associated with this item.

YUAN, Po, Tanja GAICH, 2022. Enantioselective Total Synthesis of (+)-Pepluanol A. In: Organic letters. American Chemical Society (ACS). 24, pp. 4717-4721. ISSN 1523-7060. eISSN 1523-7052. Available under: doi: 10.1021/acs.orglett.2c00961

@article{Yuan2022Enant-58032, title={Enantioselective Total Synthesis of (+)-Pepluanol A}, year={2022}, doi={10.1021/acs.orglett.2c00961}, volume={24}, issn={1523-7060}, journal={Organic letters}, pages={4717--4721}, author={Yuan, Po and Gaich, Tanja} }

<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/rdf/resource/123456789/58032"> <dcterms:issued>2022</dcterms:issued> <void:sparqlEndpoint rdf:resource="http://localhost/fuseki/dspace/sparql"/> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-07-13T14:09:21Z</dcterms:available> <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> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2022-07-13T14:09:21Z</dc:date> <dc:contributor>Gaich, Tanja</dc:contributor> <foaf:homepage rdf:resource="http://localhost:8080/jspui"/> <dcterms:isPartOf rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dc:contributor>Yuan, Po</dc:contributor> <dc:creator>Gaich, Tanja</dc:creator> <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/58032"/> <dcterms:title>Enantioselective Total Synthesis of (+)-Pepluanol A</dcterms:title> <dc:language>eng</dc:language> <dspace:isPartOfCollection rdf:resource="https://kops.uni-konstanz.de/rdf/resource/123456789/29"/> <dc:creator>Yuan, Po</dc:creator> </rdf:Description> </rdf:RDF>

This item appears in the following Collection(s)

Search KOPS


Browse

My Account