Ammonium chloride promoted three-component synthesis of 5-iminooxazoline and its subsequent transformation to macrocyclodepsipeptide.
A three-component reaction of an alpha,alpha-disubstituted alpha-isocyanoacetamide, an aldehyde and an amino alcohol afforded the 5-iminooxazoline, which, upon saponification, cyclized under acidic conditions to provide the macrocyclodepsipeptide in good overall yield.
Pirali
Tracey
T
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche and Drug and Food Biotechnology Center, Università degli Studi del Piemonte Orientale A. Avogadro, Via Bovio 6, 28100 Novara, Italy.
Tron
Gian Cesare
GC
Masson
Géraldine
G
Zhu
Jieping
J
D000081:Acetamides / Q000737:chemistry; D000143:Acids / Q000737:chemistry; D000643:Ammonium Chloride / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry; D003484:Cyanamide / Q000737:chemistry; D003500:Cyclization; D047630:Depsipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry
C526094:5-iminooxazoline; D000081:Acetamides; D000143:Acids; D002264:Carboxylic Acids; D047630:Depsipeptides; D047028:Macrocyclic Compounds; D010080:Oxazoles; D000643:Ammonium Chloride; D003484:Cyanamide