Tetrahedron

An expedient synthesis of 3-acyltetramic acids of the melophlin family from α-aminoesters and immobilized Ph 3 PCCO

R Schobert, C Jagusch

Index: Schobert, Rainer; Jagusch, Carsten Tetrahedron, 2005 , vol. 61, # 9 p. 2301 - 2307

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Citation Number: 49

Abstract

The naturally occurring 3-acyltetramic acids (3-acylpyrrolidine-2, 4-diones) melophlin A, B, C and G were prepared in few steps from α-aminoesters or their hydrochlorides by cyclization with Ph3PCCO under mild conditions. The employment of immobilized, polystyrene-bound ylide greatly simplifies the removal of by-product Ph3PO and of other impurities. Various 3- acylation methods were assessed.