Synthesis of Orthogonally Protected Labionin.

ABSTRACT: We report the first synthesis of the complex amino acid labionin in a fully orthogonally protected and stereopure form. The structure-which incorporates five orthogonal protecting groups and three stereogenic centers-was assembled using two key synthetic steps: (1) a thia-Michael addition for installing the thioether bridge; (2) an electrophilic azidation for creating the central quaternary α-amino acid carbon in a stereochemically pure form. This work is expected to enable the solid phase synthesis of both natural and synthetic analogues labyrinthopeptins.

SUBMITTER: Lo Presti E 

PROVIDER: S-EPMC9552182 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature