Activation of a terminal carboxylic acid by an internal oxazole: a novel synthesis of macrocyclodepsipeptide
A new concept for the construction of macrocyclodepsipeptides from simple and readily available starting materials has been developed. The sequence consists of (a) a three-component reaction of an aldehyde, an amino alc., and a dipeptide isocyanate and (b) a domino process involving an activation of the terminal carboxylic acid function by a built-in aminooxazole followed by a macrocyclization under acidic conditions. The synthesis is atom-economic since only a mol. of water and "MeO" is lost in the entire sequence. The overall process is also ecol. benign since LiOH and TFA are the only reagents used, while water and low-mol. wt. alc. (MeOH) are the only side products formed. [on SciFinder (R)]
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Zhao, G., Sun, X., Bienayme, H., & Zhu, J. (2001). Activation of a terminal carboxylic acid by an internal oxazole: a novel synthesis of macrocyclodepsipeptide. Journal of the American Chemical Society, 123(27), 6700–6701. https://doi.org/10.1021/ja015854d
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2001
123
27
6700
6701
CAN 135:195778
34-3
Amino Acids, Peptides, and Proteins
Institut de Chimie des Substances Naturelles,CNRS,Gif-sur-Yvette,Fr.
Journal
written in English.
100-52-7 (Benzaldehyde); 110-91-8 (Morpholine); 111-42-2; 111-71-7 (Heptanal); 156-87-6; 2508-29-4; 2937-99-7; 4048-33-3; 6688-11-5 (Cyclooctanecarboxaldehyde); 13325-10-5; 357277-74-8; 357277-75-9; 357277-76-0; 357277-77-1 Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of macrocyclodepsipeptide involving process of activation of terminal carboxylate by built-in aminooxazole and macrocyclization); 357277-78-2P; 357277-79-3P; 357277-80-6P; 357277-81-7P; 357277-82-8P; 357277-83-9P; 357277-84-0P; 357277-85-1P; 357277-86-2P; 357277-87-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. of macrocyclodepsipeptide involving process of activation of terminal carboxylate by built-in aminooxazole and macrocyclization); 357277-90-8P; 357277-91-9P; 357277-92-0P; 357277-93-1P; 357277-94-2P; 357277-95-3P; 357277-96-4P; 357277-97-5P; 357277-98-6P; 357277-99-7P; 357278-00-3P; 357278-01-4P; 357278-02-5P; 357278-03-6P; 357278-04-7P; 357278-05-8P; 357278-06-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of macrocyclodepsipeptide involving process of activation of terminal carboxylate by built-in aminooxazole and macrocyclization)
REVIEWED
OTHER