<div class="csl-bib-body">
<div class="csl-entry">Steinacher, M. (2019). <i>Towards the total synthesis of providencin</i> [Diploma Thesis, Technische Universität Wien]. reposiTUm. https://doi.org/10.34726/hss.2019.51742</div>
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dc.identifier.uri
https://doi.org/10.34726/hss.2019.51742
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/5372
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dc.description.abstract
Providencin is a highly oxygenated diterpenoid found in the sea plume Antillogorgia Kallos. It features a previously undescribed bicyclo[12.2.0]undecane carbon skeleton containing a tetrasubstituted cyclobutane ring, two trans-fused epoxides and a butenolide moiety. The absolute configuration of providencin remains to be proven. Biological testing revealed modest cytotoxic activity against several human cancer cell lines. This work presents the synthesis of an important building block en route to providencin based on a new retrosynthetic approach. Key steps are an enantioselective Lewis acid-catalyzed cycloaddition reaction to form the cyclobutane ring, a copper-assisted Stille-coupling under very mild conditions and the regioselective deprotection of just one of two trityl protecting groups.
en
dc.language
English
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dc.language.iso
en
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dc.rights.uri
http://rightsstatements.org/vocab/InC/1.0/
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dc.subject
total synthesis
en
dc.subject
providencin
en
dc.title
Towards the total synthesis of providencin
en
dc.type
Thesis
en
dc.type
Hochschulschrift
de
dc.rights.license
In Copyright
en
dc.rights.license
Urheberrechtsschutz
de
dc.identifier.doi
10.34726/hss.2019.51742
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dc.contributor.affiliation
TU Wien, Österreich
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dc.rights.holder
Michael Steinacher
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dc.publisher.place
Wien
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tuw.version
vor
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tuw.thesisinformation
Technische Universität Wien
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tuw.publication.orgunit
E163 - Institut für Angewandte Synthesechemie
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dc.type.qualificationlevel
Diploma
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dc.identifier.libraryid
AC15332099
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dc.description.numberOfPages
78
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dc.identifier.urn
urn:nbn:at:at-ubtuw:1-122704
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dc.thesistype
Diplomarbeit
de
dc.thesistype
Diploma Thesis
en
tuw.author.orcid
0000-0002-4065-9067
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dc.rights.identifier
In Copyright
en
dc.rights.identifier
Urheberrechtsschutz
de
tuw.advisor.staffStatus
staff
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item.languageiso639-1
en
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item.openairetype
master thesis
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item.grantfulltext
open
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item.fulltext
with Fulltext
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item.cerifentitytype
Publications
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item.mimetype
application/pdf
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item.openairecristype
http://purl.org/coar/resource_type/c_bdcc
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item.openaccessfulltext
Open Access
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crisitem.author.dept
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
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crisitem.author.orcid
0000-0002-4065-9067
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crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
