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Synthesis of the Threoglucin 1,3-Oxazinane Core via Cyclothreonine Rearrangement
Natalia Cano-Sampaio1, Juan R Del Valle1
1Department of Chemistry & Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, United States.
None:
Cyclization of serine and threonine-containing N-hydroxy dipeptides under Mitsunobu conditions affords 1,3-oxazinanes via N-acylimine intermediates. Synthesis of the heterocyclic core of the threoglucin family of antibiotics proceeds in high yield to afford the α-quaternary amidoketal dipeptide. The described method provides convenient entry into a new class of constrained peptides featuring Cα-heteroatom substitution.
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