Total Synthesis of the Diterpene Waihoensene

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dc.contributor.authorRosenbaum, Lisa-Catherine
dc.contributor.authorHäfner, Maximilian
dc.contributor.authorGaich, Tanja
dc.date.accessioned2020-10-21T08:47:17Z
dc.date.available2020-10-21T08:47:17Z
dc.date.issued2021-02-08
dc.description.abstractA racemic and scalable enantioselective total synthesis of (+)-waihoensene was accomplished. (+)-Waihoensene belongs to the diterpene natural product family, and it features an angular triquinane substructure motif. Its tetracyclic [6.5.5.5]backbone is all-cis-fused, containing six contiguous stereocenters, four of which are quaternary. These structural features were efficiently installed by means of a diastereoselective radical cyclization, followed by an intramolecular Pauson-Khand reaction, a diastereoselective α-alkylation, and a diastereoselective 1,4-addition reaction. Enantioselectivity was introduced at an early stage, by an asymmetric palladium catalyzed decarboxylative allylation reaction on gram scale.
dc.description.versionpublishedde
dc.identifier.doi10.1002/anie.202011298eng
dc.identifier.pmid33103334
dc.identifier.ppn1755920113
dc.identifier.urihttps://kops.uni-konstanz.de/handle/123456789/51433
dc.language.isoengeng
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subject.ddc540eng
dc.titleTotal Synthesis of the Diterpene Waihoenseneeng
dc.typeJOURNAL_ARTICLEde
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kops.citation.bibtex
@article{Rosenbaum2021-02-08Total-51433,
  year={2021},
  doi={10.1002/anie.202011298},
  title={Total Synthesis of the Diterpene Waihoensene},
  number={6},
  volume={60},
  issn={1433-7851},
  journal={Angewandte Chemie International Edition},
  pages={2939--2942},
  author={Rosenbaum, Lisa-Catherine and Häfner, Maximilian and Gaich, Tanja}
}
kops.citation.iso690ROSENBAUM, Lisa-Catherine, Maximilian HÄFNER, Tanja GAICH, 2021. Total Synthesis of the Diterpene Waihoensene. In: Angewandte Chemie International Edition. Wiley. 2021, 60(6), pp. 2939-2942. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.202011298deu
kops.citation.iso690ROSENBAUM, Lisa-Catherine, Maximilian HÄFNER, Tanja GAICH, 2021. Total Synthesis of the Diterpene Waihoensene. In: Angewandte Chemie International Edition. Wiley. 2021, 60(6), pp. 2939-2942. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.202011298eng
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