Ferrier Carbocyclization-Mediated Synthesis of Enantiopure Azido Inositol Analogues.

Azide-modified inositol (InoAz) analogues are valuable as inhibitors and have shown promise as metabolic chemical reporters (MCRs) for labeling inositol-containing glycoconjugates in eukaryotic cells and potentially in mycobacteria, but the synthesis of enantiomerically pure InoAz analogues via traditional approaches is challenging. As a complementary route, here we investigated the application of the Ferrier carbocyclization reaction to the synthesis of enantiopure InoAz analogues starting from readily available azido glucosides. Using this approach combined with a -methoxybenzyl protecting group strategy, 3-azido-3-deoxy- and 4-azido-4-deoxy-d--inositol were efficiently synthesized.