Synthesis of the Threoglucin 1,3-Oxazinane Core via Cyclothreonine Rearrangement
Abstract
-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.
Fields of Study & Subjects
Chemical Synthesis and Analysis
Microbial Natural Products and Biosynthesis
Carbohydrate Chemistry and Synthesis
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 7
- Pages
- 2295–2299
- Publication date
- 5 February 2026
- Language
- EN