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.
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