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Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy

Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy

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LEITNER, Christian, Tanja GAICH, 2017. Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy. In: Chemical Communications : ChemComm. 53(54), pp. 7451-7453. ISSN 1359-7345. eISSN 1364-548X

@article{Leitner2017Total-39623, title={Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy}, year={2017}, doi={10.1039/c7cc02699d}, number={54}, volume={53}, issn={1359-7345}, journal={Chemical Communications : ChemComm}, pages={7451--7453}, author={Leitner, Christian and Gaich, Tanja} }

<rdf:RDF xmlns:rdf="http://www.w3.org/1999/02/22-rdf-syntax-ns#" xmlns:bibo="http://purl.org/ontology/bibo/" xmlns:dc="http://purl.org/dc/elements/1.1/" xmlns:dcterms="http://purl.org/dc/terms/" xmlns:xsd="http://www.w3.org/2001/XMLSchema#" > <rdf:Description rdf:about="https://kops.uni-konstanz.de/rdf/resource/123456789/39623"> <dcterms:available rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2017-07-19T08:46:15Z</dcterms:available> <dc:contributor>Leitner, Christian</dc:contributor> <dcterms:issued>2017</dcterms:issued> <dc:date rdf:datatype="http://www.w3.org/2001/XMLSchema#dateTime">2017-07-19T08:46:15Z</dc:date> <dcterms:abstract xml:lang="eng">A total synthesis to the pseudoaspidospermidine family via a C-H activation/transannular cyclization strategy has been accomplished. The applicability of this approach is showcased in the concise synthesis (ten steps) of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine (4) starting from literature known compound 11. Via a joint synthetic sequence we were also able to address the related iboga alkaloid (±)-isovelbanamine (7) in nine steps. Key features of this synthesis are a transannular cyclization to generate the pseudoaspidospermidine skeleton (C-H activation) and a Witkop photocyclization reaction providing a 9-membered lactam. It is also worth mentioning that the joint synthetic sequence can be carried out on a multigram scale.</dcterms:abstract> <bibo:uri rdf:resource="https://kops.uni-konstanz.de/handle/123456789/39623"/> <dc:language>eng</dc:language> <dc:creator>Gaich, Tanja</dc:creator> <dc:creator>Leitner, Christian</dc:creator> <dc:contributor>Gaich, Tanja</dc:contributor> <dcterms:title>Total synthesis of (±)-20S-hydroxy-1,2-dehydro-pseudoaspidospermidine via a C–H activation/transannular cyclization strategy</dcterms:title> </rdf:Description> </rdf:RDF>

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