Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-D-ribopyranose ring system donors

Identifier:  imarina:9297387

Handle: https://hdl.handle.net/20.500.11797/imarina9297387

Authors:  Boutureira, O; Matheu, MI; Díaz, Y; Castillón, S

Abstract:
2,3-Dideoxy-D-ribopyranose units are important ring systems found in nature. Herein, we develop a metal-mediated strategy to form this important scaffold featuring a cross-metathesis reaction of the corresponding sugar-derived hydroxyalkene with electron-rich phenyl vinyl sulfide using commercially available ruthenium-catalysts under microwave irradiation as a key step. The final 2,3-dideoxyhexopyranose ring is generated in a single step upon 6-endo electrophilic cyclization.