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)]


Published in:
Journal of Organic Chemistry, 72, 5, 1826-1829
Year:
2007
Keywords:
Alcohols Role: RCT (Reactant) ; SPN (Synthetic preparation) ; PREP (Preparation) ; RACT (Reactant or reagent) (amino ; 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); Peptides Role: SPN (Synthetic preparation) ; PREP (Preparation) (depsipeptides ; cyclic; 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 macrocyclization
Note:
CAN 146:359144
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
0022-3263
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)
Laboratories:




 Record created 2010-11-25, last modified 2018-03-17


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