ArticleJournal of the American Chemical Society2023
Rapid Access to 2,2-Disubstituted Indolines via Dearomative Indolic-Claisen Rearrangement: Concise, Enantioselective Total Synthesis of (+)-Hinckdentine A.
Article in Journal of the American Chemical Society, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 31 citations in OpenAlex.
- Dearomative [3,3]-Claisen Rearrangement of 2-Indolyl Alcohols: An Efficient and General Protocol for Synthesizing 3,3-Disubstituted Indolines and Related Indole Alkaloids.Angewandte Chemie (International ed. in English) · 2026Article
- Trials into Triumphs: The Emergence of a Concise Total Synthesis of Hinckdentine A.The Journal of organic chemistry · 2026Article
- Total Synthesis of (+)-Melonine and (+)-NAngewandte Chemie (International ed. in English) · 2026Article
- Asymmetric Synthesis of the Pentacyclic Framework ofOrganic letters · 2025Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The construction of 2,2-disubstituted indolines has long presented a synthetic challenge without any general solutions. Herein, we report a robust protocol for the dearomative Meerwein-Eschenmoser-Claisen rearrangement of 3-indolyl alcohols that provides efficient access to 2-substituted and 2,2-disubstituted indolines. These versatile subunits are useful for natural product synthesis and medicinal chemistry. The title [3,3] sigmatropic rearrangement proceeds in generally excellent yield and transfers the C3-indolic alcohol chirality to the C2 position with high fidelity, thus providing a reliable method for the construction of enantioenriched 2,2-disubstituted indolines. The power of this methodology is demonstrated through the concise and strategically unique total synthesis of the marine natural product hinckdentine A, which features a dearomative Claisen rearrangement, a diastereocontrolled hydrogenation of the alkene product, a one-pot amide-to-oxime conversion using Vaska's complex, and a regioselective late-stage tribromination.
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Registered trials
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