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, 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)]
2007
72
5
1826
1829
CAN 146:359144
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
111-71-7 (Heptanal); 122-78-1 (Phenylacetaldehyde); 2043-61-0 (Cyclohexanecarboxaldehyde); 98648-05-6 (6-(N-Benzyloxycarbonylamino)hexanal); 320350-51-4; 357277-75-9; 929875-41-2 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); 811867-58-0P; 929875-33-2P; 929875-34-3P; 929875-35-4P; 929875-36-5P; 929875-37-6P; 929875-38-7P; 929875-39-8P; 929875-40-1P; 929875-42-3P; 929875-43-4P; 929875-44-5P; 929875-45-6P; 929875-46-7P; 929875-48-9P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), 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); 929875-47-8P; 929875-49-0P; 929875-50-3P; 929875-51-4P; 929875-52-5P; 929875-53-6P; 929875-54-7P; 929875-55-8P; 929875-56-9P Role: SPN (Synthetic preparation), PREP (Preparation) (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)
REVIEWED
OTHER