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.