The tetramic acid (2,4-pyrrolidin-2,4-dione) heterocycle system was found to be a key structural unit in many natural products due to its interesting biological activities.1 Tetramic acids are polar and quite unreactive; for this reason the functionalization of these heterocycles is often a difficult task. We are interested in the synthesis and the application of N-acyl 2-carboxy tetramic acids, because they may be applied to the formation of pseudopeptides foldamers, as these interesting structures are constrained amino acid mimetics, containing an endocyclic carbonyl group which forces the two exocyclic carbonyls in the trans conformation, following the same effect that we have observed for the 4-carboxy-oxazolidin-2-one.
One-pot Synthesis of Tetramic Acid Derivatives for the Preparation of beta-turn Mimics / N. Castellucci; C. Tomasini. - STAMPA. - (2011), pp. 16-16. (Intervento presentato al convegno COST Action CM0803 workshop "Foldamers: From Synthesis and Folding to Functions" tenutosi a Leeds University nel September 7th-9th 2011).
One-pot Synthesis of Tetramic Acid Derivatives for the Preparation of beta-turn Mimics
CASTELLUCCI, NICOLA;TOMASINI, CLAUDIA
2011
Abstract
The tetramic acid (2,4-pyrrolidin-2,4-dione) heterocycle system was found to be a key structural unit in many natural products due to its interesting biological activities.1 Tetramic acids are polar and quite unreactive; for this reason the functionalization of these heterocycles is often a difficult task. We are interested in the synthesis and the application of N-acyl 2-carboxy tetramic acids, because they may be applied to the formation of pseudopeptides foldamers, as these interesting structures are constrained amino acid mimetics, containing an endocyclic carbonyl group which forces the two exocyclic carbonyls in the trans conformation, following the same effect that we have observed for the 4-carboxy-oxazolidin-2-one.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
