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Open AccessArticle

Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives

1
Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech Republic
2
Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, IN 46556, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Gianfranco Favi
Molecules 2019, 24(7), 1406; https://doi.org/10.3390/molecules24071406
Received: 13 March 2019 / Revised: 4 April 2019 / Accepted: 8 April 2019 / Published: 10 April 2019
(This article belongs to the Special Issue Modern Strategies for Heterocycle Synthesis)
In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2H,5′H-[3,3′-bipyrrole]-2,5′-diones. View Full-Text
Keywords: solid-phase synthesis; ketone; traceless synthesis; natural products; enol ethers solid-phase synthesis; ketone; traceless synthesis; natural products; enol ethers
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MDPI and ACS Style

Schütznerová, E.; Krchňáková, A.; Krchňák, V. Traceless Solid-Phase Synthesis of Ketones via Acid-Labile Enol Ethers: Application in the Synthesis of Natural Products and Derivatives. Molecules 2019, 24, 1406.

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