Ammonium chloride promoted three-component synthesis of 5-iminooxazoline and its subsequent transformation to macrocyclodepsipeptide.

Tracey Pirali , Gian Cesare Tron , Géraldine Masson (1) , Jieping Zhu (1)

1 ICSN - Institut de Chimie des Substances Naturelles

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.

Domaines: Biologie cellulaire

Tracey Pirali, Gian Cesare Tron, Géraldine Masson, Jieping Zhu. Ammonium chloride promoted three-component synthesis of 5-iminooxazoline and its subsequent transformation to macrocyclodepsipeptide.. Organic Letters, 2007, 9 (25), pp.5275-5278. ⟨10.1021/ol7024372⟩. ⟨hal-00214167⟩