Solid Phase Synthesis of 3-Acyl-2,4-Pyrrolidinediones (3-Acyl Tetramic Acids) via Mild Cyclative Cleavage

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Abstract
The solid phase synthesis of 3-acyl-2,4-pyrrolidinediones (3-acyl tetramic acids) has been reported. Cyclative cleavage of the penultimate intermediative via a Dieckmann cyclization yields the 3-acyl-2,4-pyrrolidinediones. Remarkably mild conditions are required for the cyclative cleavage; treatment of the resin-bound acyclic precursor with one equivalent of potassium hydroxide in methanol at room temperature for 5-30 minutes affords the product. The synthetic route routinely provides high yields in greater than 95% purity and is compatible with acid-labile protecting groups. Virtually any hydroxy-functionalized resin can be utilized for this synthesis.

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