Raghu Vannam and Mark W. Peczuh
Org. Biomol. Chem., 2016,14, 3989-3996
DOI:
10.1039/C6OB00262E,
Paper
An efficient, seven-step synthesis of carbohydrate based oxepines is reported using per-O-acetyl septanoses as key intermediates. The scope of the synthesis was evaluated by varying both the pyranose starting materials and protecting groups incorporated into the oxepine products. The practicality of the method make it amenable to scale up as demonstrated by the gram-scale synthesis of the D-glucose derived oxepine.
