title: Benzotriazole-mediated syntheses of depsipeptides and oligoesters.
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.
authors: Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611-7200, USA.
authors: Ilker
authors: I
authors: Avan
authors: Srinivasa R
authors: SR
authors: Tala
authors: Peter J
authors: PJ
authors: Steel
authors: Alan R
authors: AR
authors: Katritzky
mesh_terms: D000215:Acylation; D000577:Amides / Q000138:chemical synthesis; D047630:Depsipeptides / Q000138:chemical synthesis*; D004952:Esters / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000577:Amides; D047630:Depsipeptides; D004952:Esters; D014230:Triazoles; C012771:benzotriazole