Rapid synthesis of cyclodepsipeptides containing a sugar amino acid or a sugar amino alcohol by a sequence of a multicomponent reaction and acid-mediated macrocyclization.
Cyclodepsipeptides incorporating a sugar amino acid (alcohol) have been synthesized. A three-component reaction of a sugar amino acid (SAA) derivative, an aldehyde, and a dipeptide isonitrile in refluxing methanol afforded the corresponding 5-aminooxazole which, after saponification, underwent a trifluoroacetic acid promoted macrocyclization to furnish the cyclic sugar amino acids.
Bughin
Carine
C
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France. zhu@icsn.cnrs-gif.fr
Masson
Géraldine
G
Zhu
Jieping
J
D000143:Acids; D000596:Amino Acids / Q000737:chemistry*; D000605:Amino Alcohols / Q000737:chemistry*; D002855:Chromatography, Thin Layer; D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D012997:Solvents; D013055:Spectrophotometry, Infrared; D013402:Sugar Alcohols / Q000737:chemistry*
D000143:Acids; D000596:Amino Acids; D000605:Amino Alcohols; D047630:Depsipeptides; D007202:Indicators and Reagents; D012997:Solvents; D013402:Sugar Alcohols