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• W4382046304 endingPage "14838" @default.
• W4382046304 startingPage "14831" @default.
• W4382046304 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." @default.
• W4382046304 created "2023-06-27" @default.
• W4382046304 creator A5022113756 @default.
• W4382046304 creator A5049114112 @default.
• W4382046304 creator A5076644899 @default.
• W4382046304 creator A5084550043 @default.
• W4382046304 date "2023-06-26" @default.
• W4382046304 modified "2023-10-14" @default.
• W4382046304 title "Rapid Access to 2,2-Disubstituted Indolines via Dearomative Indolic-Claisen Rearrangement: Concise, Enantioselective Total Synthesis of (+)-Hinckdentine A" @default.
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• W4382046304 doi "https://doi.org/10.1021/jacs.3c03611" @default.
• W4382046304 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37364288" @default.
• W4382046304 hasPublicationYear "2023" @default.
• W4382046304 type Work @default.

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