ArticleAngewandte Chemie (International ed. in English)2022
Total Synthesis of Shearinines D and G: A Convergent Approach to Indole Diterpenoids.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Gold catalysis toward the synthesis of natural products: a review.RSC advances · 2026Review
- Enantioconvergent Chan-Evans-Lam C(spJournal of the American Chemical Society · 2026Article
- Total syntheses ofChemical science · 2026Article
- Steglich esterification: A versatile synthetic approach toward the synthesis of natural products, their analogues/derivatives.Heliyon · 2024Article
- Allylic hydroxylation of enones useful for the functionalization of relevant drugs and natural products.Nature communications · 2023Article
- Total Synthesis of (+)-Shearilicine.Journal of the American Chemical Society · 2023Article
- Concise Synthesis of (-)-GAJournal of the American Chemical Society · 2023Article
- Total Synthesis of Shearinines D and G: A Convergent Approach to Indole Diterpenoids.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors.
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Abstract
The first total syntheses of the indole diterpenoids (+)-shearinine G and D are disclosed. The successful routes rely on late-stage coupling of two complex fragments. Formation of the challenging trans-hydrindane motif was accomplished by diastereoselective, intramolecular cyclopropanation. A one-pot sequence consisting of Sharpless dihydroxylation/Achmatowicz reaction was developed to install the dioxabicyclo[3.2.1]octane motif. The indenone subunit was accessed by Prins cyclization. Tuning the electronic nature of the substituents on the parent arylcarboxaldehyde allowed access to divergent products that were further transformed into shearinines G and D. Riley-type oxidation of a bicyclic enone yielded a surprising stereochemical outcome.
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