Abstract
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.
Subject
Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science
Reference46 articles.
1. Combinatorial Synthesis of Small Organic Molecules;Balkenhohl;Angew. Chem. Int. Ed.,1996
2. Solid-phase Chemistry: A Useful Tool to Discover Modulators of Protein Interactions
3. Solid-Phase Synthesis of Complex and Pharmacologically Interesting Heterocycles;Nielsen;Curr. Opin. Drug Discovery Dev.,2009
4. Solid-Phase Synthesis of Nitrogenous Heterocycles;Krchnak,2017
5. P-Alkoxybenzyl Alcohol Resin and P-Alkoxybenzyloxycarbonylhydrazide Resin for Solid Phase Synthesis of Protected Peptide Fragments;Wang;J. Am. Chem. Soc.,1973
Cited by
5 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献