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.

Carine Bughin (1) , Géraldine Masson (2) , Jieping Zhu (1, 3, 4)

1 ICSN - Institut de Chimie des Substances Naturelles
2 INCM - Institut de neurosciences cognitives de la méditerranée - UMR 6193
3 PVM (UMR_7151) - Pathologie et virologie moléculaire
4 UC Riverside - University of California [Riverside]

Cyclodepsipeptides incorporating a sugar amino acid (alcohol) have been synthesized. A three-component reaction of a sugar amino acid (SAA) derivative, an aldehyde, and a dipeptide isonitrile in refluxing methanol afforded the corresponding 5-aminooxazole which, after saponification, underwent a trifluoroacetic acid promoted macrocyclization to furnish the cyclic sugar amino acids.

Domaines: Biochimie, Biologie Moléculaire

Carine Bughin, Géraldine Masson, Jieping Zhu. 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.. Journal of Organic Chemistry, 2007, 72 (5), pp.1826-9. ⟨10.1021/jo0621874⟩. ⟨hal-00157611⟩