Synthetic strategies of phosphonodepsipeptides

Phosphonodepsipeptides are phosphorus analogues of depsipeptides and phosphonate-linked naturally occurring peptides. They more stable than phosphonopeptides have been widely applied as enzyme inhibitors, haptens for the production antibodies, biological agents, prodrugs. The synthetic strategies towards phosphonodepsipeptides reviewed, including phosphonylation hydroxy esters with phosphonochloridates, condensation phosphonic monoesters esters, alkylation 1-(alkoxycarbonyl)alkyl halides or sulfonates, multicomponent amides, aldehydes, dichlorophosphites followed by alcoholysis phosphinylation phosphonochloridites oxidation, carbene insertion N -protected amino acids 1-diazoalkylphosphonates. This review includes synthesis α-, β-, γ-phosphonodepsipeptides C-1-hydroxyalkylphosphonic acids.