ArticleAngewandte Chemie (International ed. in English)2021
Total Synthesis of the Diterpene Waihoensene.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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10 citing papers in PubMed.
- Enantioselective Iridium-Catalyzed Intramolecular Hydroarylation of (Hetero)Arene-Tethered Prochiral Diketones.Journal of the American Chemical Society · 2026Article
- Cobalt catalysis in organic synthesis: a powerful tool in the synthesis of natural products and pharmaceutically active compounds.RSC advances · 2026Review
- Advances in the Total Synthesis of Angular Triquinane-Type Natural Products.Molecules (Basel, Switzerland) · 2025Review
- Stereo-Differentiating Asymmetric Rh(I)-Catalyzed Pauson-Khand Reaction: A DFT-Informed Approach to Thapsigargin Stereoisomers.Journal of the American Chemical Society · 2025Article
- Finding activity through rigidity: syntheses of natural products containing tricyclic bridgehead carbon centers.Natural product reports · 2023Review
- Total Synthesis of Terpenes and Their Biological Significance: A Critical Review.Pharmaceuticals (Basel, Switzerland) · 2022Review
- An efficient approach to angular tricyclic molecular architecture via Nazarov-like cyclization and double ring-expansion cascade.Nature communications · 2022Article
- Total syntheses of strained polycyclic terpenes.Chemical communications (Cambridge, England) · 2022Review
- Synthetic study toward the diterpenoid aberrarone.Beilstein journal of organic chemistry · 2022Article
- Total Synthesis of the Diterpene Waihoensene.Angewandte Chemie (International ed. in English) · 2021Article
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3 authors.
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Abstract
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.
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