Tetrahedron

One-step synthesis of N-acetylcysteine and glutathione derivatives using the Ugi reaction

AG Zhdanko, AV Gulevich, VG Nenajdenko

Index: Zhdanko, Alexander G.; Gulevich, Anton V.; Nenajdenko, Valentine G. Tetrahedron, 2009 , vol. 65, # 24 p. 4692 - 4702

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Citation Number: 28

Abstract

Fully protected natural and unnatural N-acetylcysteine, dipeptide Cys–Gly, glutathione, and homoglutathione derivatives were synthesized by the Ugi four-component reaction using various benzylthio aldehydes and ketones as carbonyl building blocks. The scope and limitations of the method were investigated. Formation of imidazoline by-products in the Ugi reaction was discussed. 2, 2, 2-Trifluoroethanol was shown to be a superior reaction ...