Benzotriazole-Mediated Syntheses of Depsipeptides and Oligoesters

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

JOURNAL OF ORGANIC CHEMISTRY, cilt.76, sa.12, ss.4884-4893, 2011 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 76 Sayı: 12
  • Basım Tarihi: 2011
  • Doi Numarası: 10.1021/jo200174j
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC), Current Chemical Reactions (CCR)
  • Sayfa Sayıları: ss.4884-4893
  • Anadolu Üniversitesi Adresli: Evet

Özet

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.