A stereocontrolled synthesis of hapalosin

Abstract

A facile synthetic method for two components of hapalosin, that is, β-hydroxy-γ-amino acid and β-hydroxy acid, has been established by utilizing chiral building blocks efficiently resolved in a lipase-catalyzed transesterification. Furthermore, the synthesis of hapalosin through macrolactamization of the seco acid derived from these two components and (S)-2-hydroxy-3-methylbutyric acid has thus been demonstrated.