Total Synthesis of the Diterpene Waihoensene

Rosenbaum, Lisa-Catherine; Häfner, Maximilian; Gaich, Tanja

Total Synthesis of the Diterpene Waihoensene

Dateien

Rosenbaum_2-1rac8fgyg3t3d0.pdfGröße: 1.16 MBDownloads: 158

Datum

2021

Open Access-Veröffentlichung

Open Access Hybrid

Sammlungen

Chemie

Publikationstyp

Zeitschriftenartikel

Publikationsstatus

Published

Erschienen in

Angewandte Chemie International Edition. Wiley. 2021, 60(6), pp. 2939-2942. ISSN 1433-7851. eISSN 1521-3773. Available under: doi: 10.1002/anie.202011298

Zusammenfassung

A 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.

Fachgebiet (DDC)

540 Chemie

Zitieren

ISO 690

ROSENBAUM, 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.202011298

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}
}

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