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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Synthesis of Orthogonally Protected Labionin
Eliana Lo Presti1, Alessandro Volonterio1,2, Monica Sani1
1National Research Council, Institute of Chemical Sciences and Technologies "Giulio Natta" (SCITEC), via Mario Bianco 9, 20131 Milan, Italy.
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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