A divergent synthesis of (+)-muscarine and (+)-epi-muscarine from D-glucose

A novel stereospecific synthesis of (+)-muscarine and (+)-epi-muscarine has been achieved by utilizing d -glucose as a chiral precursor. The key steps of the synthesis involved stereospecific cyclization of 3,5-di-O-sulfonyl- d -glucofuranose derivatives into the corresponding 2,5-anhydrides, and stereospecific hydrogenation of 2,5-anhydro- l -threo-hex-2-enose ethylene acetal derivatives, thus providing an access to divergent intermediates for the preparation of both target molecules in a fully stereospecific manner.