Benzotriazole-Mediated Syntheses of Depsipeptides and Oligoesters

Avan I., Tala S. R., Steel P. J., Katritzky A. R.

JOURNAL OF ORGANIC CHEMISTRY, vol.76, no.12, pp.4884-4893, 2011 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 76 Issue: 12
  • Publication Date: 2011
  • Doi Number: 10.1021/jo200174j
  • Journal Name: JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Page Numbers: pp.4884-4893
  • Anadolu University Affiliated: Yes

Abstract

Reactions of O-Pg(alpha-hydroxyacyl)benzotriazoles with (a) unprotected alpha-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(alpha-Aminoacyl)benzotriazoles reacted with alpha-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 alpha-hydroxycarboxylic acids. O-Acylation of alpha-hydroxycarboxylic acids with N-Pg(alpha-aminoacyl)benzotriazoles followed by deprotection produced unprotected depsides useful for the preparation of depsitripeptides.