<div class="csl-bib-body">
<div class="csl-entry">Kratena, N., & Gärtner, P. (2024, September 24). <i>Bio-inspired approaches for the synthesis of complex terpenoids</i> [Conference Presentation]. Österreichische Chemietage 2024, Graz, Austria.</div>
</div>
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dc.identifier.uri
http://hdl.handle.net/20.500.12708/208314
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dc.description.abstract
Semi synthesis of structurally interesting and highly oxygenated terpenoids from more simple and available starting materials is considered one of the main areas of investigation in natural product synthesis. In our research program we investigate intriguing reactions invoked in the biosynthesis and try to mimic those transformations in the laboratory. Target reactions include for example cascade polyene cyclisations (Greenwaylactams A-C), intramolecular aldol reactions (Alstoscholarinoids A-B, see Scheme 1) as well as cationic rearrangements (Forrestiacids A-B).
Alstoscholarinoids A and B are triterpenoids with novel, rearranged carbon skeleta, which were first isolated in 2021 in extremely small quantities from the medicinal plant Alstonia scholaris. These terpenoids exhibit some intriguing biological activity (potent antihyperuricemic effects) and unique 6/6/5/6/6/6 and 6/6/6/7/5 ring systems and were therefore targeted for synthesis. The final steps in our retrosynthetic analysis were the “obvious” supposed biogenetic disconnections (purple) giving rise to key dialdehyde and 10-membered diketone. The reactions required to render the final natural products from these intermediates can suffer from some immediate selectivity issues (site of deprotonation, stereochemistry of addition) which we aimed to surpass by careful tuning of reaction conditions. In this light, the synthesis started from commercially available oleanolic acid and led to the required precursors in 5 or 8 steps longest linear sequence.
en
dc.description.sponsorship
FWF - Österr. Wissenschaftsfonds
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dc.language.iso
en
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dc.subject
Biomimetic Strategies
en
dc.subject
natural products
en
dc.subject
biosynthetic pathways
en
dc.subject
oxidations
en
dc.title
Bio-inspired approaches for the synthesis of complex terpenoids
en
dc.type
Presentation
en
dc.type
Vortrag
de
dc.relation.grantno
J4483-N
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dc.type.category
Conference Presentation
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tuw.project.title
Totalsynthese von Greenwaylactamen und Puupehenone mittels Polyene Zyklisaierungsstrategien
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tuw.researchinfrastructure
Röntgenzentrum
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tuw.researchinfrastructure
Zentrum für Kernspinresonanzspektroskopie
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tuw.researchTopic.id
M6
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tuw.researchTopic.name
Biological and Bioactive Materials
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tuw.researchTopic.value
100
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tuw.publication.orgunit
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
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tuw.author.orcid
0000-0002-3080-7214
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tuw.author.orcid
0000-0003-1569-5020
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tuw.event.name
Österreichische Chemietage 2024
de
tuw.event.startdate
23-09-2024
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tuw.event.enddate
25-09-2024
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tuw.event.online
On Site
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tuw.event.type
Event for scientific audience
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tuw.event.place
Graz
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tuw.event.country
AT
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tuw.event.institution
TU Graz
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tuw.event.presenter
Kratena, Nicolas
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tuw.event.track
Multi Track
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wb.sciencebranch
Chemie
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wb.sciencebranch
Chemische Verfahrenstechnik
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wb.sciencebranch
Pharmazie, Pharmakologie, Toxikologie
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wb.sciencebranch.oefos
1040
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wb.sciencebranch.oefos
2040
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wb.sciencebranch.oefos
3012
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wb.sciencebranch.value
60
-
wb.sciencebranch.value
20
-
wb.sciencebranch.value
20
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item.languageiso639-1
en
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item.openairetype
conference paper not in proceedings
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item.grantfulltext
none
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item.fulltext
no Fulltext
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item.cerifentitytype
Publications
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item.openairecristype
http://purl.org/coar/resource_type/c_18cp
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crisitem.author.dept
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
-
crisitem.author.dept
E163-03-3 - Forschungsgruppe Stereoselektive und nachhaltige Chemie
-
crisitem.author.orcid
0000-0002-3080-7214
-
crisitem.author.orcid
0000-0003-1569-5020
-
crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
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crisitem.author.parentorg
E163-03 - Forschungsbereich Organische und Biologische Chemie
