Bughin, CarineMasson, GeraldineZhu, Jieping2010-11-252010-11-252010-11-25200710.1021/jo0621874https://infoscience.epfl.ch/handle/20.500.14299/58437Cyclodepsipeptides incorporating a sugar amino acid, e.g., I, have been synthesized. A three-component reaction of a sugar amino acid (SAA) deriv., an aldehyde, and a dipeptide isonitrile in refluxing methanol afforded the corresponding 5-aminooxazole which, after sapon., underwent a trifluoroacetic acid promoted macrocyclization to furnish the cyclic sugar amino acids. [on SciFinder (R)]Alcohols Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (aminosugar; prepn. of cyclodepsipeptides via three-component cyclocondensation of sugar amino acid or sugar amino alc. with aldehydes and isonitriles followed by macrocyclization as key steps); Peptides Role: SPN (Synthetic preparation)PREP (Preparation) (depsipeptidescyclic; prepn. of cyclodepsipeptides via three-component cyclocondensation of sugar amino acid or sugar amino alc. with aldehydes and isonitriles followed by macrocyclization as key steps); Cyclocondensation reaction; Macrocyclization (prepn. of cyclodepsipeptides via three-component cyclocondensation of sugar amino acid or sugar amino alc. with aldehydes and isonitriles followed by macrocyclization as key steps); Aldehydes Role: RCT (Reactant)RACT (Reactant or reagent) (prepn. of cyclodepsipeptides via three-component cyclocondensation of sugar amino acid or sugar amino alc. with aldehydes and isonitriles followed by macrocyclization as key steps); Amino acids Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (sugar; prepn. of cyclodepsipeptides via three-component cyclocondensation of sugar amino acid or sugar amino alc. with aldehydes and isonitriles followed by macrocyclization as key steps); Multicomponent reaction (three-component; prepn. of cyclodepsipeptides via three-component cyclocondensation of sugar amino acid or sugar amino alc. with aldehydes and isonitriles followed by macrocyclization as key steps)cyclodepsipeptide prepn; sugar amino acid aldehyde isonitrile three component cyclocondensation macrocyclizationRapid synthesis of cyclodepsipeptides containing a sugar amino acid or a sugar amino alcohol by a sequence of a multicomponent reaction and acid-mediated macrocyclizationtext::journal::journal article::research article