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Ruthenium-catalyzed cross-metathesis with electron-rich phenyl vinyl sulfide enables access to 2,3-dideoxy-d-ribopyranose ring system donors†
Omar Boutureira,M. Isabel Matheu,Yolanda Díaz,Sergio Castillón
RSC Advances Pub Date : 04/16/2014 00:00:00 , DOI:10.1039/C4RA01668H
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.

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