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Synlett 1998; 1998(12): 1341-1342
DOI: 10.1055/s-1998-1973
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Solid Phase Synthesis of 3-Acyl-2,4-Pyrrolidinediones (3-Acyl Tetramic Acids) via Mild Cyclative Cleavage

Todd T. Romoff* , Liang Ma, Yongwen Wang, David A. Campbell
  • *Division of Chemistry, Affymax Research Institute, 3410 Central Expressway, Santa Clara, CA 95051; Fax (408) 481-0522; E-mail: todd_romoff@affymax.com
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Publication Date:
31 December 2000 (online)

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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.

tetramic acids - cyclative cleavage - Dieckmann cyclization - solid phase synthesis - combinatorial libraries