Benzotriazole-mediated syntheses of depsipeptides and oligoesters

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

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23 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)4884-4893
Number of pages10
JournalJournal of Organic Chemistry
Volume76
Issue number12
DOIs
StatePublished - Jun 17 2011

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