A straightforward route to hydantocidin analogues with pyranose ring structure

Article abstract of DOI:10.1016/S0040-4020(97)00213-5

Partial hydrolysis of the nitrile moiety in aeetylated 1-bromo-glycopyranosyl cyanides 1 and 9 mediated by TiCl₄ gave C-(1-bromo-1-deoxy-glycopyranosyl) formamides 2 and 10 whose reaction either with AgOCN, AgSCN or KSCN in nitromethane resulted in the formation of glycopyranosylidene-spirohydantoins 3, 11 and 15 and -thiohydantoins 7 and 16. Zemplen-deacetylation gave the pyranoid epihydantocidin analogues 4 and 12, and thiohydantocidin analogues 8 and 17, respectively.