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

Molecules

Anna Krchňáková¹  Eva Schütznerová²  Viktor Krchňák² 

[1] Department of Chemistry and Biochemistry, 251 Nieuwland Science Center, University of Notre Dame, Notre Dame, IN 46556, USA;Department of Organic Chemistry, Faculty of Science, Palacký University, 17. listopadu 12, 771 46 Olomouc, Czech Republic;

关键词: solid-phase synthesis;    ketone;    traceless synthesis;    natural products;    enol ethers;   

DOI  :  10.3390/molecules24071406

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown