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 stere ospecific hydrogenation of 2,5-anhydro-L-threo-hex-2-enose ethylene acetal derivatives, thus providing an access to divergent intermediates for the pr eparation of both target molecules in a fully stereospecific manner. (C) 20 00 Elsevier Science Ltd. All rights reserved.