Benzotriazole-mediated syntheses of depsipeptides and oligoesters.

Ilker Avan, Srinivasa R Tala, Peter J Steel, Alan R Katritzky

Index: J. Org. Chem. 76 , 4884-4893, (2011)

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Abstract

Reactions of O-Pg(α-hydroxyacyl)benzotriazoles with (a) unprotected α-hydroxycarboxylic acids, (b) amino acids, and (c) amines afforded, respectively, chirally pure (a) oligoesters, (b) depsidipeptides, and (c) amide conjugates (yields 52-94%). N-Pg(α-Aminoacyl)benzotriazoles reacted with α-hydroxycarboxylic acids to yield depsidipeptides (47-87%). N-Pg(depsidipeptidoyl)benzotriazoles, obtained from depsidipeptides, gave depsitripeptides (yields 55-78%) on reaction with amino acids and α-hydroxycarboxylic acids. O-Acylation of α-hydroxycarboxylic acids with N-Pg(α-aminoacyl)benzotriazoles followed by deprotection produced unprotected depsides useful for the preparation of depsitripeptides.